Methanol → Methyl 3-cyclohexyl-1H-indole-6-carboxylate

HRID 272545노트

반응식

HRID 272545 반응식
S(Cl)(Cl)=O.[CH:5]1([C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:23]O>>[CH:5]1([C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 112419893-cyclohexyl-1H-indole-6-carboxylic Acid

생성물 1

HCID 11230631Methyl 3-cyclohexyl-1H-indole-6-carboxylate수율 69%

실험 절차

Thionyl chloride (1 mL) was added to a stirred mixture of 3-cyclohexyl-1H-indole-6-carboxylic acid (30.4 g, 0.125 mol) in methanol (300 mL). The mixture was stirred at reflux for 18 hours, treated with decolorizing carbon, and filtered. The filtrate was concentrated to about 150 mL at which point crystallization occurred. The filtrate was cooled to room temperature and filtered. The solid washed with cold methanol followed by diethyl ether to provide the desired product as a pale purple solid (22.2 g, 69% yield). ESI-MS m/z 258 (MH+); 1H NMR (300 MHz, CDCl3.) δ 1.35 (m, 4H), 1.63 (s, 1H), 1.78 (m, 3H), 2.06 (d, J=8.05 Hz, 2H, 3.90 (m, 1H), 7.08 (d, J=1.83 Hz, 1H), 7.62 (s, 1H), 7.65 (s, 1H), 7.74 (d, J=1.46 Hz, 1H), 7.77 (d, J=1.46 Hz, 1H), 8.08 (s, 1H).

후처리

  1. temperatureat reflux for 18 hours
  2. additiontreated with decolorizing carbon
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to about 150 mL at which point crystallization
  5. filtrationfiltered
  6. washThe solid washed with cold methanol

출처 및 근거

ORD 기록
ord-99bbf6c8dc92492ea2bd42350a2e72a6
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456167B2

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