반응 #90366

반응 방정식

5-bromonicotinic acid

oxalyl chloride

NaHCO3

cyclopropylmethanamine

→

5-bromo-N-(cyclopropylmethyl) nicotinamide

수율 71.1%

용매

DCM

DMF

반응 조건

후처리

1. 1
   기타The 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
   추출extracted with DCM
5. 5
   건조The combined organic phases were dried over MgSO4
6. 6
   농축concentrated
7. 7
   기타dried under vacuum

실험 절차

To a solution of 5-bromonicotinic acid (XXVIII) (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 (XXIX) 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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