Acetic acid, azido-, ethyl ester → ethyl 5-bromo-6-methoxy-1H-indole-2-carboxylate

HRID 400729ノート

反応式

HRID 400729 の反応式
CC[O-].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=O.[N:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N+]=[N-]>CCO>[Br:5][C:6]1[CH:7]=[C:8]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[NH:16][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9]2

参加物

5

反応物 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 986623-Bromo-4-methoxybenzaldehydeHCID 2723922Sodium ethoxide

生成物 1

HCID 14916489ethyl 5-bromo-6-methoxy-1H-indole-2-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of sodium ethylate in ethanol (prepared from sodium (1.92 g; 83.70 mmol) and EtOH (40 mL)) was added dropwise to a cold (−10° C.) solution of 3-bromo-p-anisaldehyde (4 g; 18.60 mmol) and ethyl azidoacetate (ABCR, 27.80 ml; 46.50 mmol) in EtOH (60 mL). After the end of the addition, the reaction mixture was warmed up to 0° C. and stirred at RT for 5 hours. The heterogenous mixture was poured onto ice and stirred for 30 minutes. The solid was collected by filtration and dried under high vacuum. The solid was taken up in xylenes (60 mL) and heated to reflux for 3 hours. The solvent was evaporated and the residue was purified by silica column chromatography (c-Hexane/ethyl acetate, 80/20) to give the title compound as a pale yellow solid. 1H NMR (DMSO-d6) δ 11.87 (s, 1H), 7.89 (s, 1H), 7.05 (s, 1H), 6.98 (s, 1H), 4.31 (q, J=7 Hz, 2H), 3.85 (s, 3H), 1.32 (t, J=7 Hz, 3H). HPLC (Method A), Rt 4.28 min (Purity: 98.1%). LC/MS (Method B): 297.2 (M+H)+.

後処理

  1. additionAfter the end of the addition
  2. additionThe heterogenous mixture was poured onto ice
  3. stirringstirred for 30 minutes
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum
  6. temperatureheated
  7. temperatureto reflux for 3 hours
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica column chromatography (c-Hexane/ethyl acetate, 80/20)

出典と根拠

ORDレコード
ord-31cfe72e145c442c9af98cb8cdb4e709
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

反応ノート

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