Methanol → N-((2-bromopyridin-4-yl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide

HRID 1662206노트

반응식

HRID 1662206 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]([S:23]([NH2:25])=[O:24])([CH3:22])[CH3:21].CO>C1COCC1.C(=O)(O)[O-].[Na+].[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=[N:25][S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])[CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 887MethanolHCID 3382465Tert-ButanesulfinamideHCID 585795282-(2-Bromopyridine-4-carbonyl)-6-fluorobenzonitrile

생성물 1

HCID 76821597N-((2-bromopyridin-4-yl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide수율 67.5%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 516892Sodium Bicarbonate촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-(2-bromopyridine-4-carbonyl)-6-fluorobenzonitrile (3.0 g, 9.8 mmol) in dry THF (60 mL) was added to a solution of titanium (IV) ethoxide (8.0 mL, 38.6 mmol) in dry THF (20 mL) at room temperature. 2-Methyl-2-propanesulfinamide (1.8 g, 14.7 mmol) was then added in one portion and the reaction mixture was heated at reflux temperature for 40 hours. The reaction mixture was cooled to room temperature and methanol (10 mL) was added, followed by saturated sodium bicarbonate solution (10 drops). The mixture was stirred at room temperature for 1 hour, filtered through a pad of sodium sulfate, and the solids were washed thoroughly with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (20-50% ethyl acetate in hexanes) to afford the title compound (2.7 g, 67.5%).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 40 hours
  3. filtrationfiltered through a pad of sodium sulfate
  4. washthe solids were washed thoroughly with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by flash column chromatography (20-50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-bfe6f0cb4dbf42329226c39ad3b6c241
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030500B2

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