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Cesium carbonate → 5'-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid ethyl ester

HRID 1678476
ノート
印刷プレビュー

反応式

HRID 1678476 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:10]2[CH:9]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20])[CH:13]=[CH:12][C:11]=2[O:14][C:15]([F:18])([F:17])[F:16])=[CH:28][CH:27]=1)=[O:25])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 59822358(3-Bromo-4-trifluoromethoxy-phenyl)-carbamic acid tert-butyl ester

生成物 1

HCID 598223825'-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid ethyl ester収率 72.8%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane
溶媒

実験手順

A mixture of (3-bromo-4-trifluoromethoxy-phenyl)-carbamic acid tert-butyl ester (250 mg), 4-ethoxycarbonyl-phenyl boronic acid (136 mg), cesium carbonate (228 mg) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (15 ml) was heated to reflux for 18 h. The mixture was then cooled and partitioned between water and ethyl acetate. The dried extracts were evaporated and the residue purified on silica gel. Elution with 5-40% ethyl acetate:petrol gave a pale yellow solid (217 mg)

後処理

  1. temperatureto reflux for 18 h
  2. temperatureThe mixture was then cooled
  3. custompartitioned between water and ethyl acetate
  4. customThe dried extracts were evaporated
  5. customthe residue purified on silica gel
  6. washElution with 5-40% ethyl acetate

出典と根拠

ORDレコード
ord-85c230e72c5d4aa19212fe0cb61dab78
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008303B2

反応ノート

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