Bromoacetonitrile → HCID 86670824, compound

HRID 878365Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]([F:24])([F:23])[F:22])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:29][C:30]#[N:31]>CN(C=O)C>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:29][C:30]#[N:31])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]([F:22])([F:23])[F:24])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of [4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (190 mg, 0.54 mmol) in DMF (5 mL) was added sodium hydride (24 mg, 0.59 mmol, 60% dispersion in mineral oil) at 0° C. The reaction mixture was stirred at 25° C. for 30 minutes. Then bromoacetonitrile (71 mg, 0.59 mmol) was added to the reaction mixture and it was stirred at 25° C. for 24 hours. The reaction mixture was quenched with 10 mL saturated NH4Cl solution and extracted with EtOAc (2×40 mL). The combined EtOAc part was dried over Na2SO4 and evaporated. The residue crude was purified by silica gel column chromatography eluting with a gradient of n-hexane:EtOAc (85:15 to 70:30) to get the desired compound as a light yellow sticky liquid (185 mg, 88%). LC-MS (ESI): m/z=394.4 [M+H]+.

Workup

stirringwas stirred at 25° C. for 24 hours
customThe reaction mixture was quenched with 10 mL saturated NH4Cl solution
extractionextracted with EtOAc (2×40 mL)
dry with materialThe combined EtOAc part was dried over Na2SO4
customevaporated
customThe residue crude was purified by silica gel column chromatography
washeluting with a gradient of n-hexane:EtOAc (85:15 to 70:30)

Sources & evidence

ORD record: ord-8f91fbeab6fa40998f016341dec10308
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987307B2

Reaction notes

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