Hydrochloric Acid → 2-(1,2-Dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 55966

Reaction equation

C([Si](C)(C)[O:6][CH2:7][C:8]([C:11]1[N:12](S(C)(=O)=O)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=2)([OH:10])[CH3:9])(C)(C)C.[OH-].[Na+].Cl>CO.O>[OH:10][C:8]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[C:15]([C:22]([F:25])([F:23])[F:24])[CH:14]=2)([CH3:9])[CH2:7][OH:6]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 2-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-ethyl]-1-methanesulfonyl-6-trifluoromethyl-1H-indole-5-carbonitrile (9.22 g, 0.01935 mole) in methanol (150 mL), a solution of NaOH (4.64 g 0.1161 mole) in water (25 mL) was added. The resulting mixture was heated in an oil-bath at 50° C. for 4 hr and then stirred at room temperature overnight. To the reaction mixture was then added 1 N HCl until the pH was 3. The aqueous mixture was extracted with EtOAc, the organic layer was washed with water, brine, then dried over MgSO4. The solvent was stripped off, the residue was triturated with DCM, and the resulting solid collected by filtration to yield the title compound as a light grey solid.

Workup

extractionThe aqueous mixture was extracted with EtOAc
washthe organic layer was washed with water, brine
dry with materialdried over MgSO4
customthe residue was triturated with DCM
filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record: ord-dc1202a34df044749dc07d22a6d732f4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434688B2

Linked notes

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