4-(benzyloxy)-7-bromo-5-fluoro-1H-indole → 2-(4-(benzyloxy)-7-bromo-5-fluoro-1H-indol-3-yl)acetic acid

HRID 1404141Notes

Reaction equation

HRID 1404141 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[C:14]2[C:10]=1[C:11]([CH2:21][C:22]([OH:24])=[O:23])=[CH:12][N:13]2C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(F)=CC(Br)=C2C=1C=CN2)C1C=CC=CC=1>ClCCl.CO>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[C:14]2[C:10]=1[C:11]([CH2:21][C:22]([OH:24])=[O:23])=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 583038564-(benzyloxy)-7-bromo-5-fluoro-1H-indoleHCID 583040362-(4-(benzyloxy)-7-bromo-5-fluoro-1-methyl-1H-indol-3-yl)acetic acid

Product 1

HCID 583038972-(4-(benzyloxy)-7-bromo-5-fluoro-1H-indol-3-yl)acetic acidYield 58%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following the procedure (step 3, scheme 33) used to prepare compound 33-4, compound 17-1 gave compound 34-2 in 58% yield as a yellow solid after column chromatography on silica gel eluting with dichloromethane/methanol (5:1). LRMS: calc 377.0 and found: 378.0 [M+1].

Sources & evidence

ORD record
ord-e55f0157675240cea71a03970661c355
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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