Triethylamine → N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

HRID 44243

반응식

HRID 44243 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])([O-:19])=[O:18]>O1CCCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[N+:17]([O-:19])=[O:18])[C:5]([Cl:8])=[N:6][CH:7]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

생성물 1

HCID 86658034N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 5-bromo-2-chloropyridine-3-amine (3.9 g, 18.9 mmol) and triethylamine (5.3 mL, 37.9 mmol) in tetrahydrofuran (60 mL) was added 2-nitrobenzoylchloride (2.49 mL, 18.9 mmol). The reaction was stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate (60 mL). The organic layer was separated and washed with water (50 mL), brine (50 mL), dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes). The N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide was obtained as a yellow solid (1.5 g). LCMS [M+H]: 356.

후처리

  1. customThe organic layer was separated
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-ab89fc2dc2b24ffea8f46cdcfcbc29fa
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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