Water → Ethyl 1-ethyl-1H-indole-3-carboxylate

HRID 1695236Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[CH2:16](I)[CH3:17].O.[CH2:20]1COCC1>CCOC(C)=O>[CH2:3]([O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH3:17])[CH:8]=1)=[O:6])[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of NaH (50-60% dispersion in mineral oil, 548.0 mg, 11.4 mmol, 2.0 eq) in THF (20 mL), 1H-indole-3-carboxylic acid methyl ester (1.0 g, 5.7 mmol, 1.0 eq) was added and after 20 min also ethyl iodide (507.0 μL, 6.3 mmol, 1.1. eq) was added. The reaction was heated at 70° C. for 1 h. The mixture was cooled down to 0° C. and water (10 mL) was added carefully. AcOEt was added and the organic phase was collected and concentrated, to give the crude compound that was purified through SiO2 column (10 g) with gradient elution from 100% cyclohexane to cyclohexane-EtOAc 80:20. The title product (860 mg, 74% yield) was obtained.

Workup

additionwas added
temperatureThe mixture was cooled down to 0° C.
customthe organic phase was collected
concentrationconcentrated
customto give the crude compound that
customwas purified through SiO2 column (10 g) with gradient elution from 100% cyclohexane to cyclohexane-EtOAc 80:20

Sources & evidence

ORD record: ord-3a15594ca3104e32b037fa2d69c89555
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163729B2

Reaction notes

Loading…