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

HRID 57318

反応式

HRID 57318 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-863bbacc59ae4f1498b0036fe5995fc5
出典データセット
uspto-grants-2016_09
特許番号
US09434724B2

関連ノート

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