反应 #1135850

反应方程式

5-bromonicotinic acid

oxalyl chloride

NaHCO3

cyclopropylmethanamine

→

5-bromo-N-(cyclopropylmethyl)nicotinamide

收率 71.1%

溶剂

DCM

DMF

反应条件

后处理

1. 1
   其他The solvent was evaporated under vacuum
2. 2
   workup.ADDITIONbefore adding dry pyridine (10 mL)
3. 3
   workup.STIRRINGThe solution was stirred at r.t. under nitrogen for 2 h
4. 4
   萃取extracted with DCM
5. 5
   干燥The combined organic phases were dried over MgSO4
6. 6
   浓缩concentrated
7. 7
   其他dried under vacuum

实验过程

To a solution of 5-bromonicotinic acid (XVI) (1.01 g, 5 mmol) in dry DCM (10 mL) under nitrogen was added oxalyl chloride (0.654 mL, 7.5 mmol) followed by dry DMF (0.1 mL). The solution was stirred at r.t. for 30 min. The solvent was evaporated under vacuum before adding dry pyridine (10 mL) followed by cyclopropylmethanamine (0.39 mL, 4.5 mmol). The solution was stirred at r.t. under nitrogen for 2 h. The solution was poured into ice water, basified with sat. aq. NaHCO3 and extracted with DCM. The combined organic phases were dried over MgSO4, concentrated and dried under vacuum to yield 5-bromo-N-(cyclopropylmethyl)nicotinamide (XVII) as an off-white solid (0.82 g, 3.2 mmol, 71% yield). 1H NMR (DMSO-d6) δ ppm −0.07-0.07 (m, 2H), 0.15-0.29 (m, 2H), 0.68-0.88 (m, 1H), 2.93 (t, J=6.22 Hz, 2H), 8.20 (t, J=1.88 Hz, 1H), 8.62 (d, J=1.70 Hz, 2H), 8.75 (s, 1H); ESIMS found C10H11BrN2O m/z 254, 256 (M+, M+2).

来源