Реакция #1135850

Уравнение реакции

5-bromonicotinic acid

oxalyl chloride

NaHCO3

cyclopropylmethanamine

→

5-bromo-N-(cyclopropylmethyl)nicotinamide

Выход 71.1%

Растворители

DCM

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe 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
   Экстракцияextracted with DCM
5. 5
   СушкаThe combined organic phases were dried over MgSO4
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеdried under vacuum

Методика

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).

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