Dichloromethane → Ethyl 6-(benzenesulphonylmethyl)-3-cyclopropyl-2-methoxybenzoate

HRID 2177708ノート

反応式

HRID 2177708 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[CH:26]1(B(O)O)[CH2:28][CH2:27]1.C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH:26]3[CH2:28][CH2:27]3)=[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 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66762321Cyclopropylboronic acid monohydrateHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2 回

生成物 1

HCID 67107983Ethyl 6-(benzenesulphonylmethyl)-3-cyclopropyl-2-methoxybenzoate収率 59.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
140 °C

実験手順

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.347 g), cyclopropyl boronic acid monohydrate (0.087 g), palladium chloride dppf adduct with DCM (0.07 g) and cesium carbonate (0.8 g) in THF (9 ml) and water (1 ml) was sealed in a microwave vial and degassed. The mixture was then heated in the microwave at 140° C. for 15 minutes. After cooling, the mixture was dried (MgSO4) and filtered through Celite. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of t-butyl methyl ether and cyclohexane with a gradient from 0-60% to give ethyl 6-(benzenesulphonylmethyl)-3-cyclopropyl-2-methoxybenzoate (0.187 g) as a gum.

後処理

  1. customwas sealed in a microwave vial and
  2. customdegassed
  3. temperatureAfter cooling
  4. dry with materialthe mixture was dried (MgSO4)
  5. filtrationfiltered through Celite
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of t-butyl methyl ether and cyclohexane with a gradient from 0-60%

出典と根拠

ORDレコード
ord-b7404bc897aa4ef1a3572ee1afd28f7c
出典データセット
uspto-grants-2015_06
特許番号
US09067905B2

反応ノート

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