Ethyl indole-2-carboxylate → HCID 68577987, compound

HRID 642729Notes

Reaction equation

HRID 642729 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].Br[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH3:27])[CH:20]=[CH:19][CH:18]=1>>[CH2:13]([O:12][C:10]([C:2]1[N:1]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[CH3:27])[CH:20]=[CH:19][CH:18]=2)[C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[CH3:14]

Participants

3

Reactant 2

HCID 73125Ethyl indole-2-carboxylateHCID 14931580HCID 14931580, compound

Product 1

HCID 68577987HCID 68577987, compound

Procedure

Using general procedure A (Exp. 1.3.), 1,8-dimethyl-naphthalene was reacted with N-bromosuccinimide to give 1-bromomethyl-8-methyl-naphthalene as white solid. MS: 234.1 ([M]+). Using general procedure B, ethyl 2-indole carboxylate was coupled with 1-bromomethyl-8-methyl-naphthalene to give 1-(8-methyl-naphthalen-1-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give the title compound as a white solid. MS: 314.4 ([M−H]−).

Sources & evidence

ORD record
ord-edf2a363e82649198eca07b71cf39f58
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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