Application of 155310-11-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 155310-11-5, name is 3-Amino-2,2-difluoropropan-1-ol, molecular formula is C3H7F2NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: To a solution of 4-chloro-1-fluoro-2-nitro-benzene (2.6 mmol)and amine (2.6 mmol), K2CO3 (5.2 mmol) in DMF (10 mL) wasadded TEA (5.2 mmol). The mixture was then stirred at 100 C for2 h. After the reaction was complete, the mixture was poured intowater (30 mL) and extracted with EtOAc (30 mL) three times. Thecombined organic layer was washed with brine (20 mL), dried overNa2SO4 and then concentrated in vacuo. The residue was thenpurified by column chromatography on silica gel to give 4-chloro-N(R2)-2-nitro-aniline. To a solution of 4-chloro-N(R2)-2-nitro-aniline (2.2 mmol) andhydrazine hydrate (1 mL) in the mixed solvent of MeOH (5 mL) andTHF (5 mL) was added Raney Ni (5%e10% loading). The mixturewasthen stirred at room temperature for 1-2 h. LC-MS showed completeconversion of start material. The mixture was then filteredand the filtrate was concentrated in vacuo to give the crude of 4-chloro-N1(R2)-benzene-1,2-diamine, which was used in the nextstep without further purification. A mixture of 4-chloro-N1(R2)-benzene-1,2-diamine (1 mmol)and sodium chloroacetate (130 mg, 1.1 mmol) in 4N HCl was heatedto 100 C overnight. After the reaction was complete, the mixturewas concentrated in vacuo to remove the solvent and the residuewas dissolved in DCM (100 mL). The solutionwas thenwashed withsat NaHCO3 (50 mL), brine, dried over MgSO4 and concentrated invacuo. The residue was purified by column chromatography onsilica gel (DCM/EA 3/1) to give 5-chloro-2-(chloromethyl)-1-R2-benzimidazole.To a mixture of 3-methylsulfonyl-1H-pyrazolo[3,4-c]pyridine(0.89 mmol) and 5-chloro-2-(chloromethyl)-1-R2-benzimidazole(0.74 mmol) in DMF (5 mL) was added K2CO3 (204 mg,1.48 mmol) and the mixture was stirred at rt overnight. After thereaction was completed, the mixture was filtered and the filtratewas purified by preparative HPLC to give final product. To a mixture of 3-methylsulfonyl-1H-pyrazolo[3,4-c]pyridine(0.89 mmol) and 5-chloro-2-(chloromethyl)-1-R2-benzimidazole(0.74 mmol) in DMF (5 mL) was added K2CO3 (204 mg,1.48 mmol) and the mixture was stirred at rt overnight. After thereaction was completed, the mixture was filtered and the filtratewas purified by preparative HPLC to give final product.
According to the analysis of related databases, 155310-11-5, the application of this compound in the production field has become more and more popular.
Reference:
Article; Feng, Song; Li, Chao; Chen, Dongdong; Zheng, Xiufang; Yun, Hongying; Gao, Lu; Shen, Hong C.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 1147 – 1157;,
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