2-Bromoacetamide → 2-[5-Cyano-2-ethyl-4-(trifluoromethyl)-1H-indol-1-yl]acetamide

HRID 1188459Notes

Reaction equation

[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]#[N:17])=[CH:7][CH:6]=2)[CH3:2].Br[CH2:19][C:20]([NH2:22])=[O:21]>CC#N>[C:16]([C:8]1[C:9]([C:12]([F:15])([F:13])[F:14])=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:19][C:20]([NH2:22])=[O:21])[C:3]([CH2:1][CH3:2])=[CH:11]2)#[N:17]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Ethyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.004 g, 0.018 mmol) Cs2CO3 (0.051 g, 0.16 mmol), and 2-bromoacetamide (0.022 g, 0.16 mmol) were combined in CH3CN (3 mL) and heated at 90° C. under N2 for 1 hr. Extraction with Et2O and washing with water and brine was followed by drying (Na2SO4), filtration, and concentration in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.020 g): MS (ESI): m/z 296 (M+1).

Workup

extractionExtraction with Et2O
washwashing with water and brine
customby drying
filtration(Na2SO4), filtration, and concentration in vacuo
customPurification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record: ord-3149bc879a534d679bab611f2e729f73
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673948B2

Reaction notes

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