Tetrahydrofuran → 4-(3,4-dimethoxy-phenyl)1H-indole

HRID 1820902노트

반응식

HRID 1820902 반응식
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].O1CCCC1>C(=O)([O-])[O-].[K+].[K+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[CH:5][NH:6]3)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 6764944-BromoindoleHCID 27347023,4-Dimethoxyphenylboronic acid

생성물 1

HCID 225616844-(3,4-dimethoxy-phenyl)1H-indole

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 11430Potassium Carbonate용매

반응 조건

온도
100 °C

실험 절차

In a microwave safe tube, 4-Bromoindole (1.383 g, 0.007054 mol), 3,4-dimethoxyphenyl boronic acid (3.21 g, 0.0176 mol), and Tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.00035 mol) were mixed in 1.00 M of Potassium carbonate in Water (21 mL) and Tetrahydrofuran (34 mL, 0.42 mol). The resulting mixture was heated at 100° Celsius in the microwave for 10 minutes. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the organic layers were combined, washed with brine and dried over sodium sulfate. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to the yield 1.02 g of the titled compound as a light green solid. MS(ESI) [M+H+]+=254.20.

후처리

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to the yield 1.02 g of the titled compound as a light green solid

출처 및 근거

ORD 기록
ord-0f8dd41578184aafb2b5468724efc012
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605168B2

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