Dimethylformamide → 5-bromo-4-chloro-2-(3-cyano-propoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 1848645Notes

Reaction equation

CN(C=O)C.[Br:6][C:7]1[C:8]([Cl:26])=[CH:9][C:10]([OH:25])=[C:11]([CH:24]=1)[C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:15])=[O:13].Br[CH2:28][CH2:29][CH2:30][C:31]#[N:32].C([O-])([O-])=O.[K+].[K+]>ClCCl>[Br:6][C:7]1[C:8]([Cl:26])=[CH:9][C:10]([O:25][CH2:28][CH2:29][CH2:30][C:31]#[N:32])=[C:11]([CH:24]=1)[C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:15])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring DMF solution (6 mL) containing 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg, 0.81 mmol) was added 4-bromo-butyronitrile (0.096 mL, 0.97 mmol) and K2CO3 (223 mg, 1.62 mmol). The mixture was heated at 50° C. for 8 hrs. Additional 0.5 eq. of 4-bromobutyronitrile and 0.5 eq of K2CO3 were added and the mixture was heated for another 8 hrs. The mixture was diluted with dichloromethane, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography to afford 5-bromo-4-chloro-2-(3-cyano-propoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide (241 mg). MS [M+H]+: 439.1; tR=2.62 min (method 1)

Workup

temperaturethe mixture was heated for another 8 hrs
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified via silica gel flash column chromatography

Sources & evidence

ORD record: ord-39a5140f36d749458284dfd6f8c14475
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952161B2

Reaction notes

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