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

HRID 1879121ノート

反応式

HRID 1879121 の反応式
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

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 59760055HCID 59760055、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a2a63743711c4534a499535c8a10ca59
出典データセット
uspto-grants-2012_11
特許番号
US08314147B2

反応ノート

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