Ethyl Acetate → HCID 68756369, compound

HRID 1615596Notes

Reaction equation

[S:1]1[CH:5]=C[C:3]([CH2:6][NH:7][C:8]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=2[C:10]#[N:11])=[CH:2]1.[CH3:20]C(C)([O-])C.[K+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[C:31]([O:30][C:28]([C:27]1[N:7]([C:6]2[CH:3]=[CH:2][S:1][CH:5]=2)[C:8]2[C:9]([C:10]=1[NH2:11])=[C:12]([CH3:20])[C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-[(thiophen-3-yl-methyl)amino]-5-trifluoromethylbenzonitrile 1C (1.42 g, 5.04 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) and anhydrous N,N-dimethylformamide (DMF) (10 mL) at 0° C. was added potassium tert-butoxide (1.13 g, 10.1 mmol). The reaction mixture was stirred at 0° C. for 5 minutes and tert-butyl bromoacetate 1D (1.47 g, 7.54 mmol) was added. The reaction mixture was stirred at room temperature overnight. Ethyl acetate (100 mL) was added and the organic layer was washed with 1 N hydrochloric acid and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to provide 3-amino-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1E (1.74 g, 4.39 mmol).

Workup

stirringThe reaction mixture was stirred at room temperature overnight
washthe organic layer was washed with 1 N hydrochloric acid and brine
dry with materialThe organic layer was dried over sodium sulfate
customThe organic solvent was evaporated under reduced pressure
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-297e693066ab4e30910635bb45bfd5a6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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