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

HRID 1678476
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HRID 1678476 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane
용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-85c230e72c5d4aa19212fe0cb61dab78
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008303B2

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