3-ethoxycarbonylmethyl-5-fluoro-1H-indole-2-carboxylic acid ethyl ester → 3-ethoxycarbonylmethyl-5-fluoro-1-(7-fluoro-naphthalen-1-ylmethyl)-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]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][C:11]([F:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([F:34])[CH:32]=2)[CH:27]=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([F:34])[CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][C:11]([F:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
3
Procedure
Using general procedure B, 3-ethoxycarbonylmethyl-5-fluoro-1H-indole-2-carboxylic acid ethyl ester (Lit. 10) was coupled with 1-bromomethyl-7-fluoro-naphthalene (from Example 49.3.) to give 3-ethoxycarbonylmethyl-5-fluoro-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 3-carboxymethyl-5-fluoro-1-(7-fluoro-naphthalen-1-ylmethyl)-1H-indole-2-carboxylic acid as a white solid. MS: 394.1 ([M−H]−).
Sources & evidence
- ORD record
- ord-4c7ed841dda544c9acc74143006ffe95
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696240B2
Reaction notes
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