Triethylamine → N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

HRID 40652

반응식

HRID 40652 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:16]2[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=[C:12]([Br:11])[CH:17]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 596134182-Bromo-4-chloro-5-nitropyridine

생성물 1

HCID 56926468N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine수율 77.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of 2-bromo-4-chloro-5-nitropyridine (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6-DMSO, 400 MHz) δ 9.00 (br t, 1H, J=6.3 Hz), 8.80 (s, 1H), 7.35 (d, 2H, J=8.7 Hz), 7.10 (s, 1H), 6.95 (d, 2H, J=8.8 Hz), 4.60 (d, 2H, J=6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt=2.13 min; m/z (ESI−) 336, 338 (M−H).

후처리

  1. washwas then washed successively with water and brine
  2. concentrationbefore being concentrated in vacuo to a light brown oil which

출처 및 근거

ORD 기록
ord-2e3d4c2515ea484f98336fd06b5114a8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530468B2

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