反应详情

1.32 mL (17.63 mmol) of formalin solution (37% in water) and 443 mg (7.05 mmol) of sodium cyanoborohydride were added to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 20 mL of acetonitrile, the mixture was acidified to pH 4 with HOAc, and stirred for 16 hours at RT. The reaction mixture was acidified with 4M aqueous HCl and stirred for 1 hour at RT. It was made alkaline with sat. aqueous sodium carbonate solution and the aqueous phase was exhaustively extracted with DCM. The combined organic phases were dried over magnesium sulfate and evaporated down in vacuo. The residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0). Yield: 0.24 g (46% of theoretical); C12H10BrClN2 (M=297.578); calc.: molpeak (M+H)+: 297/299/301 (BrCl); found: molpeak (M+H)+:297/299/301 (BrCl); HPLC-MS: 6.09 minutes (method B).

1. stirringstirred for 1 hour at RT
2. extractionthe aqueous phase was exhaustively extracted with DCM
3. dry with materialThe combined organic phases were dried over magnesium sulfate
4. customevaporated down in vacuo
5. customThe residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0)
6. custom6.09 minutes (method B)