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

HRID 2177708노트

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HRID 2177708 반응식
[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

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66762321Cyclopropylboronic acid monohydrateHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
140 °C

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-b7404bc897aa4ef1a3572ee1afd28f7c
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067905B2

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