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

HRID 494060ノート

反応式

HRID 494060 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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 was 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, CDC3) 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).

後処理

  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 was washed with cold methanol

出典と根拠

ORDレコード
ord-d222127b6bb345fb9a9035a23f4220ef
出典データセット
uspto-grants-2009_05
特許番号
US07538102B2

反応ノート

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