methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylate → 1-(7-fluoro-naphthalen-1-ylmethyl)-3-methoxycarbonylmethyl-1H-indole-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].Br[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=2)[CH:24]=[CH:23][CH:22]=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[C:7]2[C:12]([C:13]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]Participants
3
Procedure
Using general procedure B, 3-methoxycarbonylmethyl-1H-indole-2-carboxylic acid methyl ester (prepared according to Lit. 2) was coupled with 1-bromomethyl-7-fluoro-naphthalene (from Example 49.3.) to give 1-(7-fluoro-naphthalen-1-ylmethyl)-3-methoxycarbonylmethyl-1H-indole-2-carboxylic acid methyl ester which was hydrolyzed as described in the general procedure B (Exp. 2.2) to the title compound as a white solid. MS: 375.9 ([M−H]−).
Sources & evidence
- ORD record
- ord-1bbef65b608c4c1bb1804541e39717ed
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696240B2
Reaction notes
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