ethyl 5-methyl-1H-indole-2-carboxylate → 1-(7-fluoro-naphthalen-1-ylmethyl)-5-methyl-1H-indole-2-carboxylic acid ethyl ester
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]([CH3:15])=[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]([CH3:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
3
Procedure
Using general procedure B, 5-methyl-1H-indole-2-carboxylic acid ethyl ester was coupled with 1-bromomethyl-7-fluoro-naphthalene (from Example 49.3.) to give 1-(7-fluoro-naphthalen-1-ylmethyl)-5-methyl-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: 332.3 ([M−H]−).
Sources & evidence
- ORD record
- ord-47020f33b9d64314812f31955bd0d8bb
- Source dataset
- uspto-grants-2010_04