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

HRID 272545Notes

Reaction equation

HRID 272545 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-99bbf6c8dc92492ea2bd42350a2e72a6
Source dataset
uspto-grants-2008_11
Patent number
US07456167B2

Reaction notes

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