Sodium hydride → 1-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

HRID 968636Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[C:12]([OH:14])=[O:13].[H-].[Na+].Br[CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O.O>[CH:19]1([CH2:18][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[CH:4][C:3]=3[O:2][CH3:1])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

7-Methoxyindole-3-carboxylic acid (3.0 g, 16.6 mmol) was added portionwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.56 g, 39 mmol) in dimethylformamide (75 ml). After 1 h, bromomethylcyclohexane (5.7 g, 32.3 mmol) was added. The mixture was heated to 60° C. with stirring for 1 h. The mixture was diluted with water (250 ml) and washed with ethyl acetate and then diethyl ether. The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off. The crude product was recrystallised from ethyl acetate to afford 1-(cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (3.75 g) as a crystalline solid.

Workup

washwashed with ethyl acetate
filtrationthe precipitate filtered off
customThe crude product was recrystallised from ethyl acetate

Sources & evidence

ORD record: ord-6a8c084de2884a29ac699250b4a8a484
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304064B2

Reaction notes

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