Dimethyl Sulfoxide → ethyl 2-methyl-1H-indole-3-carboxylate

HRID 1526949

反応式

HRID 1526949 の反応式
CS(C)=O.I[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12].O=[C:14]([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu-]=O.O>[CH3:21][C:14]1[NH:12][C:7]2[C:6]([C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=2

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8868Ethyl AcetoacetateHCID 10796Cesium carbonateHCID 119952-Iodoaniline

生成物 1

HCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate収率 15.1%

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a mixed solution of dimethyl sulfoxide and water (20 mL), 2-iodobenzenamine (3.0 g, 13.7 mmol), ethyl 3-oxobutanoate (2.0 g, 15.1 mmol), copper(I) oxide (0.2 g, 1.4 mmol) and cesium carbonate (4.5 g, 13.7 mmol) was added. The mixture was stirred at 100° C. for 9 hours under nitrogen gas atmosphere. The reaction mixture was filtered through a pad of celite. The filtrate was diluted with water and extracted with ethyl acetate. The organic phase was concentrated in vacuo, and then the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give ethyl 2-methyl-1H-indole-3-carboxylate as a light yellow solid (0.42 g, 15%). 1H NMR (300 MHz, CDCl3): δ 8.12-8.09 (m, 1H), 7.31-7.16 (m, 3H), 4.40 (q, J=6.9 Hz, 2H), 2.77 (s, 3H), 1.45 (t, J=6.9 Hz, 3H).

後処理

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. additionThe filtrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated in vacuo
  5. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-bb1e46f6229547b2979abf4b7300b792
出典データセット
uspto-grants-2015_07
特許番号
US09085583B2

関連ノート

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