Tetrabutylammonium Fluoride → HCID 136016240, compound

HRID 2078730Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[C:10]([Br:25])=[C:9]1[C:26]1[C:27]2[S:40][CH:39]=[CH:38][C:28]=2[N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([Br:25])=[C:9]1[C:26]1[C:27]2[S:40][CH:39]=[CH:38][C:28]=2[N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:30]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-bromo-2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester [0.32 g, 49 mmol, Intermediate (64)] in tetrahydrofuran at 0° C. was added a 1.0 M TBAF solution in tetrahydrofuran (0.51 mL, 0.51 mmol). The resulting solution was stirred at 0° C. for 30 minutes. The solvent was removed. The residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 95/05 as eluant) to produce 3-bromo-2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-hydroxy-indole-1-carboxylic acid tert-butyl ester [0.22 g, 83%, Intermediate (65)] as an orange foam.

Workup

customThe solvent was removed
customThe residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 95/05 as eluant)

Sources & evidence

ORD record: ord-ee52f6af9bdd4d6ab8abdee930a0f30f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928231B2

Reaction notes

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