Ethanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester

HRID 1844634노트

반응식

HRID 1844634 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)=[CH:4][C:3]=1[CH3:25].[C:26]([O-:29])(=[O:28])C.[Na+].[C]=O.[CH2:33](O)[CH3:34]>CN(C)C=O.ClCCl.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:33]([O:29][C:26](=[O:28])[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:14])([F:16])[F:15])[CH:10]=[N:9]2)=[CH:4][C:3]=1[CH3:25])[CH3:34]

참가 물질

7

반응물 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 866589832-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrroleHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 672174284-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester

시약·촉매·용매 2

HCID 178478475HCID 178478475, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(4-bromo-3-methyl-phenyl)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrole (Example 14) (7.0 g) in a mixture of ethanol (60 ml) and dimethylformamide (20 ml), was added dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane adduct (“Pd(dppf)Cl2”) (0.8 g) and sodium acetate (1.4 g) at ambient temperature. The reaction mixture was stirred in a pressure reactor in an atmosphere of carbon monoxide (6 bar) at 85° C. for 16 hours. The reaction mixture was cooled to ambient temperature, the ethanol was evaporated and aqueous sodium hydrogen carbonate (saturated) (200 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: gradient of 0-4% v/v methanol in dichloromethane) to give 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid ethyl ester (2.8 g). 1H-NMR (CDCl3, 400 MHz): 8.04-7.06 (m, 7H), 5.46-5.06 (m, 1H), 4.35 (m, 2H), 3.27-3.79 (m, 1H), 2.59 (m, 3H), 2.38-2.10 (m, 1H), 1.39 (m, 3H) ppm.

후처리

  1. customthe ethanol was evaporated
  2. additionaqueous sodium hydrogen carbonate (saturated) (200 ml) and ethyl acetate (250 ml) were added
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent

출처 및 근거

ORD 기록
ord-f7aa16bd60d94146ab8fb9ec00b85fd4
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946447B2

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