Ethyl 4-methoxy-1H-indole-2-carboxylate → 1-(7-fluoro-naphthalen-1-ylmethyl)-4-methoxy-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)=[C:12]([O:15][CH3:16])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=2)[CH:22]=[CH:21][CH:20]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([F:29])[CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH3:16])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]Participants
3
Procedure
Using general procedure B, 4-methoxy-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)-4-methoxy-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: 348.3 ([M−H]−).
Sources & evidence
- ORD record
- ord-5b668250de254676820d72561747b6f2
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696240B2
Reaction notes
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