Tetrabutylammonium Fluoride → 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxy-indole-1-carboxylic acid tert-butyl ester

HRID 2078685Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanoxy)-indole-1-carboxylic acid tert-butyl ester (320 mg, 0.56 mmol, Example 5C) in tetrahydrofuran (5 mL) at 0° C. is added TBAF (1.0 M in tetrahydrofuran, 0.67 mL, 0.67 mmol). The solution is stirred at 0° C. for 30 minutes. The solvent is then removed and the residue is chromatographed through silica gel (dichloromethane-ethyl acetate, 95:05 to 90:10 as eluant) to produce 205 mg (80%) 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxy-indole-1-carboxylic acid tert-butyl ester as an orange foam. LC/MS: RT=3.74 minutes, 456.0 m/e.

Workup

customThe solvent is then removed
customthe residue is chromatographed through silica gel (dichloromethane-ethyl acetate, 95:05 to 90:10 as eluant)

Sources & evidence

ORD record: ord-7e62b2ee4423462fbc2d5d95d09cedea
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928231B2

Reaction notes

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