Indole → 4,5-dimethyl-1H-indole-3-carboxylic acid

HRID 57316

반응식

HRID 57316 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CB(O)O.[C:14]([O-:17])([O-])=[O:15].[K+].[K+].O1[CH2:25][CH2:24]OCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:6][C:5]1[C:24]([CH3:25])=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3]([C:14]([OH:17])=[O:15])=[CH:2][NH:1]2

참가 물질

6

반응물 4

HCID 798IndoleHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 139377Methylboronic Acid

생성물 1

HCID 570574164,5-dimethyl-1H-indole-3-carboxylic acid수율 91.8%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

반응 조건

온도
90 °C

실험 절차

A mixture of bromide 1 (1.0 g, 4.78 mmol), methyl boronic acid (860 mg, 14.3 mmol), Pd(dppf)2Cl2 (194 mg, 0.239 mmol), and K2CO3 (1.32 g, 9.56 mmol) in dioxane (20 mL) was degassed and stirred at 90° C. for 5 h under nitrogen. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography (EtOAc/petroleum ether=1/4) to give the desired product (636 mg, 4.39 mmol, 91.8%) as a white solid.

후처리

  1. customwas degassed
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel chromatography (EtOAc/petroleum ether=1/4)

출처 및 근거

ORD 기록
ord-bc86db76d4f148378e7240faa3b5a944
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434724B2

연결된 노트

불러오는 중…