Methyl indole-6-carboxylate → Methyl indoline-6-carboxylate

HRID 1808324Notes

Reaction equation

[BH3-]C#N.[Na+].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1>C(O)(=O)C>[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

NaCNBH3 (11.49 g; 0.04 equiv.) was added at 0° C., over a period of 10 minutes, to a solution of methyl 1H-indole-6-carboxylate (8 g; 1 equiv.) in acetic acid (80 ml). The reaction mixture was stirred at 0° C. for 20 minutes and then warmed to room temperature and stirred for 1 hour at room temperature. When the conversion was complete, the acetic acid was distilled off under reduced pressure and the resulting residue was dissolved in dichloromethane. The resulting phases were separated. The organic phase was washed with 1N sodium hydroxide solution and dried over sodium sulfate. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel, 10-15% ethyl acetate/hexane). Methyl indoline-6-carboxylate (6 g; 75%) was obtained in the form of a solid.

Workup

temperaturewarmed to room temperature
stirringstirred for 1 hour at room temperature
distillationthe acetic acid was distilled off under reduced pressure
dissolutionthe resulting residue was dissolved in dichloromethane
customThe resulting phases were separated
washThe organic phase was washed with 1N sodium hydroxide solution
dry with materialdried over sodium sulfate
customAfter removal of the solvent
customunder reduced pressure, purification

Sources & evidence

ORD record: ord-2edd3167dc1e442990a2bf6d96214c6b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357717B2

Reaction notes

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