Tetrabutylammonium Fluoride → 3-{6-Chloro-7-fluoro-1-[1-(2-hydroxy-ethyl)-1H-pyrazol-4-yl]-2-methyl-1H-indol-3-ylsulfanyl}-benzoic acid ethyl ester

HRID 1466941Notes

Reaction equation

HRID 1466941 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[C:16]([F:22])[C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH2:29][O:30][Si](C(C)(C)C)(C)C)[CH:27]=3)[C:13]=2[CH3:38])[CH:6]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[C:16]([F:22])[C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH2:29][OH:30])[CH:27]=3)[C:13]=2[CH3:38])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667652093-(1-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-4-yl}-6-chloro-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

Product 1

HCID 667654553-{6-Chloro-7-fluoro-1-[1-(2-hydroxy-ethyl)-1H-pyrazol-4-yl]-2-methyl-1H-indol-3-ylsulfanyl}-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(1-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-4-yl}-6-chloro-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester (0.125 g, 0.21 mmol) in THF (2 mL) at room temperature was added TBAF (0.30 mL of a 1.0 M solution in THF, 0.30 mmol). The mixture was stirred for and additional 5 minutes, then subjected to standard aqueous workup to afford the title compound.

Sources & evidence

ORD record
ord-6552c1e521ba495e848f1a0ae6cf098d
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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