Potassium Carbonate → N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

HRID 2108755노트

반응식

HRID 2108755 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13](Br)[S:12][CH:11]=1)=[O:9].CC1(C)C(C)(C)OB([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCOC(C)=O.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13]([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([S:36]([C:39]3[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:28]=2)[S:12][CH:11]=1)=[O:9]

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 497589593-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57421982N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide

생성물 1

HCID 57633172N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide수율 45%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide (100 mg, 0.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (122 mg, 0.3 mmol), potassium carbonate (125 mg, 0.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (20 mg) were combined in 4 mL DME, 1 mL water, and heated to 160° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and water. The organic layer was filtered through celite and concentrated to an oil which was purified by column chromatography on silica (20 to 60% EtOAc/hexanes) to give the product as a brown oil, 0.07 g, 0.14 mmol, 45% yield. MH+ 518.0

후처리

  1. filtrationThe organic layer was filtered through celite
  2. concentrationconcentrated to an oil which
  3. customwas purified by column chromatography on silica (20 to 60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-802ff1787b58405e8e331d338c9c74da
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514448B2

반응 노트

불러오는 중…