Category: 873697-68-8

Application of 873697-68-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 873697-68-8, name is 3-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 Step 2. A solution of 3B in dichloromethane (about 1.5 M 3B in DCM) at RT under nitrogen mixture was cooled to ~0C, and 2.0 eq of IM diisobutyllithiumaluminum hydride (DIBAlH) in DCM was added drop wise over -3.5 hours, maintaining an internal reaction temperature < 00C. Upon completion of the DiBAlH addition, the reaction mixture was added dropwise with vigorous stirring to a cooled solution (-00C) of 40 volumes of 15% Rochelle salt and 10 volumes of DCM, maintaining an internal reaction temperature below 100C. The flask was rinsed with 10 volumes of DCM and the mixture was allowed to warm to room temperature and stirred for 4 hours. The layers were separated, and the aqueous layers were back extracted with 20 volumes of DCM. The combined organic layers were washed with 20 volumes of water. The organic layer was dried over sodium sulfate and concentrated to afford a brown foam, which was dried under vacuum (-30 in Hg) at RT to afford 3C (92% yield). Example 3 Step 3A/B. A solution 1 eq of 3C, tetrahydrofuran (about 1.4 M 3C in THF) and 1.05 eq of methyl piperazine-1-carboxylate and was allowed to stir at ambient temperature for 3 hours. To the reaction mixture was added 1.5 eq of sodium triacetoxyborohydride portionwise over -40 min, maintaining an internal reaction temperature below 45C. The reaction mixture was stirred overnight at room temperature. To the reaction mixture was added 5 volumes of water dropwise, over 1 hour, maintaining an internal reaction temperature below 300C. Ethyl acetate (EtOAc, 5 volumes) was then added, and the layers were separated. The aqueous layers were back extracted with 5 volumes of EtOAc. The combined organic layers were washed with saturated sodium bicarbonate and solid sodium bicarbonate was added as needed to bring the pH to 8 (pHydrion papers). The layers were separated, and the organic layer was washed with 5 volumes of brine. The organic layer was dried over sodium sulfate and activated carbon was added in the drying step. The organics were filtered through celite and the celite pad was rinsed 4 times with EtOAc. The organics were concentrated and dried overnight on the rotavap (~30 in Hg at RT) to afford an amber-brown oil. Step 3C. All calculations are based on the amount of 3C (R= O).[0146] To 3 volumes of methanol (based on 3C, R=O)under N2 over an an ice/brine/acetone bathwas added3 eq of acetyl chloride dropwise over 3 hours, maintaining an internal reaction temperature below 00C. The solution was then stirred for an additional 1 hour below 00C. A solution of 1.0 eq of unpurified 3D (from Steps 3 A/3B above) in MeOH (about 3.6 M based on 3C, R=O) was added dropwise over 30 min, maintaining an internal reaction temperature below 15C..The reaction was allowed to warm to room temperature overnight. The solids were filtered the next day and rinsed with 2x 0.5 volumes of MeOH, 5 volumes of 1:1 rerf-butyl methyl ether (MTBE):MeOH, and 5 volumes of MTBE.[0147] The solids were then taken up in 5 volumes of EtOAc and saturated sodium bicarbonate and solid sodium bicarbonate were added as needed to bring the pH of the aqueous layer to 8 (pHydrion papers). The layers were separated, and the aqueous layer was extracted with 5 volumes of EtOAc. The combined organic layers were washed with 5 volumes of brine, dried over sodium sulfate, and concentrated to afford a pale orange solid which was dried under vacuum (-30 in Hg) at ~40C to afford 3D (50% yield). In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CYTOKINETICS, INC.; WO2007/78839; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 873697-68-8, name is 3-Amino-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H5FN2

A solution of 3B in dichloromethane (about 1.5 M 3B in DCM) at RT under nitrogen mixture was cooled to ~0C, and 2.0 eq of IM diisobutyllithiumalurninum hydride (DEB AlH) in DCM was added dropwise over -3.5 hours, maintaining an internal reaction temperature < 0C. Upon completion of the DiBAlH addition, the reaction mixture was added dropwise with vigorous stirring to a cooled solution (~0C) of 40 volumes of 15% Rochelle salt and 10 volumes of DCM, maintaining an internal reaction temperature below 100C. The flask was rinsed with 10 volumes of DCM and the mixture was allowed to warm to room temperature and stirred for 4 hours. The layers were separated, and the aqueous layers were back extracted with 20 volumes of DCM. The combined organic layers were washed with 20 volumes of water. The organic layer was dried over sodium sulfate and concentrated to afford a brown foam, which was dried under vacuum (-30 in Hg) at RT to afford 3C (92% yield). The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future. Reference:
Patent; CYTOKINETICS, INC.; WO2007/70683; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 873697-68-8, A common heterocyclic compound, 873697-68-8, name is 3-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 3; Step 2; A solution of 3B in dichloromethane (about 1.5 M 3B in DCM) at RT under nitrogen mixture was cooled to 0 C., and 2.0 eq of 1M diisobutyllithiumaluminum hydride (DIBAlH) in DCM was added dropwise over 3.5 hours, maintaining an internal reaction temperature 0 C. Upon completion of the DiBAlH addition, the reaction mixture was added dropwise with vigorous stirring to a cooled solution (0 C.) of 40 volumes of 15% Rochelle salt and 10 volumes of DCM, maintaining an internal reaction temperature below 10 C. The flask was rinsed with 10 volumes of DCM and the mixture was allowed to warm to room temperature and stirred for 4 hours. The layers were separated, and the aqueous layers were back-extracted with 20 volumes of DCM. The combined organic layers were washed with 20 volumes of water. The organic layer was dried over sodium sulfate and concentrated to afford a brown foam, which was dried under vacuum (30 in Hg) at RT to afford 3C (92% yield).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Morgan, Bradley Paul; Muci, Alex; Lu, Pu-Ping; Kraynack, Erica Anne; Tochimoto, Todd; Morgans, David J.; US2006/14761; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 873697-68-8,Some common heterocyclic compound, 873697-68-8, name is 3-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 28; 4-(3-(4-(Dimethylamino)benzamido)-2-fluoro henyl)-7-morpholino-9H- yrido[3,4-; 1. N-(3-Cyano-2-fluorophenyl)-4-(dimethylamino)benzamide; To a mixture of 3-amino-2-fluorobenzonitrile (2.24 g, 16.46 mmol) and 4- (dimethylamino)benzoyl chloride (3.46 g, 18.84 mmol) in 1,2-dichloroethane (50 mL) at rt was added pyridine (0.891 mL, 11.02 mmol). The resulting mixture was heated at 70 C for 5 hr. On cooling to room temperature, the mixture was diluted with ethyl acetate (250 mL), washed with water (5 x 60 mL) and brine (60 mL), and dried over anhydrous MgSO4. The organic solution was concentrated under vacuum, and the residue was subjected to ISCO (2 x 330 g silica gel, 25-50% ethyl acetate/hexane) to afford the desired product (4.11 g, 14.51 mmol, 88% yield) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; DELUCCA, George V.; BATT, Douglas G.; LIU, Qingjie; WO2011/159857; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 873697-68-8,Some common heterocyclic compound, 873697-68-8, name is 3-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To 3-amino-2- fluorobenzonitrile (0.5 g, 3.67 mmol) in DCM (10 mL) cooled to 0 C, was added pyridine (1 mL) and methyl chloroformate (0.313 mL, 4.04 mmol). After 24 h, the reaction was quenched with 0 (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with IN HC1 (20 mL), brine (20 mL) and dried (MgS04) to afford 0.7 g (98%) of 18A as brown solid. MS (ESI) m/z: 195.2 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts