ethyl 5-fluoro-3-formyl-1H-indole-2-carboxylate → 5-fluoro-1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester

HRID 642723Notes

Reaction equation

HRID 642723 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:15]=[O:16])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:19][C:20]1[C:21]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:22]=2[S:23][CH:24]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]2[C:21]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:22]=3[S:23][CH:24]=2)[C:8]2[C:13]([C:14]=1[CH:15]=[O:16])=[CH:12][C:11]([F:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 4352190ethyl 5-fluoro-3-formyl-1H-indole-2-carboxylateHCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiophene

Product 1

HCID 866131975-fluoro-1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester

Procedure

Using general procedure B, 5-fluoro-3-formyl-1H-indole-2-carboxylic acid ethyl ester was coupled with 3-bromomethyl-5-fluoro-benzo[b]thiophene (Lit. 18) to give 5-fluoro-1-(5-fluoro-benzo[b]thiophen-3-ylmethyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester as white solid. MS: 400.1 ([M+H]+).

Sources & evidence

ORD record
ord-3f144c7a7b174ba390f561bc684ae216
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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