Ethyl 5-chloroindole-2-carboxylate → 5-chloro-1-(7-fluoro-naphthalen-1-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 642705Notes

Reaction equation

HRID 642705 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=2)[CH:21]=[CH:20][CH:19]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 156574201-(Bromomethyl)-7-fluoronaphthalene

Product 1

HCID 685780805-chloro-1-(7-fluoro-naphthalen-1-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

Procedure

Using general procedure B, 5-chloro-1H-indole-2-carboxylic acid ethyl ester was coupled with 1-bromomethyl-7-fluoro-naphthalene (from Example 49.3.) to give 5-chloro-1-(7-fluoro-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: 352.2 ([M−H]−).

Sources & evidence

ORD record
ord-fe2ef3e83e0b4b518181d24321e2dabb
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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