Indole → 4,6-dimethyl-1H-indole-3-carboxylic acid

HRID 57318

반응식

HRID 57318 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=C[CH:8]=2)[CH:3]=[CH:2]1.[CH3:10]B(O)O.[C:14]([O-:17])([O-])=[O:15].[Cs+].[Cs+].O1[CH2:25][CH2:24]OCC1>O.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]>[CH3:10][C:5]1[CH:6]=[C:24]([CH3:25])[CH:8]=[C:9]2[C:4]=1[C:3]([C:14]([OH:17])=[O:15])=[CH:2][NH:1]2

참가 물질

7

반응물 4

HCID 798IndoleHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 139377Methylboronic Acid

생성물 1

HCID 824047364,6-dimethyl-1H-indole-3-carboxylic acid수율 40.9%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회

반응 조건

온도
110 °C

실험 절차

A mixture of indole 5 (690 mg, 3.28 mmol), methylboronic acid (495 mg, 3.94 mmol, 1.2 eq.), Pd(dppf)Cl2 (180 mg, 0.656 mmol, 0.2 eq.) and Cs2CO3 (3.20 g, 9.84 mmol, 3.0 eq.) in dioxane (21 mL) and water (3 mL) was stirred at 110° C. overnight under N2. The mixture was diluted with water and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=5/1) to give the desired product (170 mg, 1.17 mmol, 40.9%) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (petroleum ether/EtOAc=5/1)

출처 및 근거

ORD 기록
ord-863bbacc59ae4f1498b0036fe5995fc5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434724B2

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