Cesium carbonate → HCID 21252717、化合物

HRID 1895711ノート

反応式

HRID 1895711 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 57083831-Bromo-3,3,3-trifluoroprop-1-ene

生成物 1

HCID 21252717HCID 21252717、化合物収率 74.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-(benzyloxy)phenylboronic acid (1026 mg, 4.50 mmol, Alfa Aesar), (E)-1-bromo-3,3,3-trifluoroprop-1-ene (262 mg, 1.5 mmol, SynQuest), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (122 mg, 0.15, Combiphos Catalysts, Inc.) and cesium carbonate (2444 mg, 7.50 mmol, Aldrich) in Water (0.5 mL) and DMF (3.0 mL) was heated under microwave conditions (90° C., 20 min). The reaction mixture was diluted with EtOAc and filtered. The filtrate was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) to yield the title compound (310 mg, 74%) as a pale yellow solid.

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-f39619d0b8fa4293ac7f38ff6864c40a
出典データセット
uspto-grants-2013_08
特許番号
US08513424B2

反応ノート

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