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

HRID 400729노트

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HRID 400729 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-31cfe72e145c442c9af98cb8cdb4e709
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741923B2

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