Boron tribromide → Ethyl (4-{[(6-chloro-2-fluoro-3-hydroxyphenyl)carbonyl]amino}phenyl)acetate

HRID 1879121노트

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HRID 1879121 반응식
B(Br)(Br)Br.[CH2:5]([O:7][C:8](=[O:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[C:21]([O:26]C)[C:20]=2[F:28])=[O:18])=[CH:12][CH:11]=1)[CH3:6]>ClCCl>[Cl:25][C:24]1[C:19]([C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][C:8]([O:7][CH2:5][CH3:6])=[O:29])=[CH:15][CH:14]=2)=[O:18])=[C:20]([F:28])[C:21]([OH:26])=[CH:22][CH:23]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 59760055HCID 59760055, 화합물

생성물 1

HCID 59163346Ethyl (4-{[(6-chloro-2-fluoro-3-hydroxyphenyl)carbonyl]amino}phenyl)acetate수율 32.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Boron tribromide (393 μl, 4.16 mmol) was added dropwise to a solution of ethyl[4-({[6-chloro-2-fluoro-3-(methyloxy)phenyl]carbonyl}amino)phenyl]acetate (506 mg, 1.39 mmol) in dichloromethane (30 ml) at −78° C. under argon and the reaction was stirred overnight whilst slowly warming to 0° C. The reaction was quenched by the careful addition of water, stirred for 1 hour, further diluted with ethyl acetate, filtered, phases separated, the organic layer dried (Na2SO4) and solvent evaporated and the residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→80% ethyl acetate/petrol, clean fractions collected) to afford the title compound as a colourless foam (157 mg, 32%).

후처리

  1. customThe reaction was quenched by the careful addition of water
  2. stirringstirred for 1 hour
  3. additionfurther diluted with ethyl acetate
  4. filtrationfiltered
  5. customphases separated
  6. dry with materialthe organic layer dried (Na2SO4) and solvent
  7. customevaporated
  8. customthe residue purified by flash chromatography (Biotage SP4, 25+M silica column, 0→80% ethyl acetate/petrol, clean fractions collected)

출처 및 근거

ORD 기록
ord-a2a63743711c4534a499535c8a10ca59
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314147B2

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