Cesium carbonate → Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate

HRID 1778357ノート

反応式

HRID 1778357 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30]([C:32]1[O:33][CH:34]=[CH:35][C:36]=1B1OC(C)(C)C(C)(C)O1)=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C(OCC)(=O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14]([C:36]3[CH:35]=[CH:34][O:33][C:32]=3[CH:30]=[O:31])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 164141993-(Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehydeHCID 66685058Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxy-acetylamino)benzoate2 回

生成物 1

HCID 86684734Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate収率 99.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

A mixture of tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxyacetylamino)benzoate (Intermediate 36, 0.165 g), 2-formylfuran-3-boronic acid pinacol ester (0.091 g), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride DCM complex (0.028 g) and cesium carbonate (0.311 g) in THF (4.3 mL) and water (0.7 mL) were sealed, under nitrogen, in a microwave vial and heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was diluted with ethyl acetate and water and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate (0.17 g).

後処理

  1. customwere sealed, under nitrogen, in a microwave vial
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-f0db9ef8174347119d8834e12899a61b
出典データセット
uspto-grants-2016_02
特許番号
US09266896B2

反応ノート

読み込み中…