Cesium carbonate → 3-{2-Cyano-5-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-phenoxy}-N-ethyl-N-phenyl-benzamide

HRID 379069Notes

Reaction equation

F[C:2]1[CH:9]=[C:8]([C:10]([OH:18])([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)[CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:19]([N:21]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1)[CH3:20].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]([OH:18])([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)[CH3:11])=[CH:9][C:2]=1[O:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:22]([N:21]([CH2:19][CH3:20])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30])#[N:5]

Participants

Conditions

Temperature: 60 °C

Procedure

2-Fluoro-4-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-benzonitrile (0.054 g, 0.220 mmol), N-ethyl-3-hydroxy-N-phenyl-benzamide (0.053 g, 0.220 mmol) and Cs2CO3 (0.143 g, 0.440 mmol) were dissolved in anhydrous DMF (5 mL) and heated at 60° C. under Ar for 4 days. The reaction was diluted with EtOAc, washed with satd. NaHCO3 solution, water, and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (1-3% MeOH/CH2Cl2) to give the title compound. FAB MS (M+1)=467.

Workup

washwashed with satd
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-0c9349abab454dbf82aa759d3ea12309
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297239B1

Reaction notes

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