Cesium carbonate → 4-Imidazol-1-ylmethyl-2-[2-(2-oxo-2H-pyridin-1-yl)-phenoxy]-benzonitrile

HRID 379074Notes

Reaction equation

HRID 379074 reaction equation
F[C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:16]=[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:11]1([CH2:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[O:16])[CH:9]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 216970562-(2-oxo-2H-pyridin-1-yl)-phenolHCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

Product 1

HCID 99511524-Imidazol-1-ylmethyl-2-[2-(2-oxo-2H-pyridin-1-yl)-phenoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile (as described in Example 9, Step E) (0.0276 g, 0.137 mmol), 2-(2-oxo-2H-pyridin-1-yl)-phenol (0.0257 g, 0.137 mmol) and cesium carbonate (0.089 g, 0.274 mmol) were combined in DMF (1.2 mL) and heated at 70° C. for 18 hr. The title compound was obtained after RP HPLC on aWaters Prep Pak column eluting with a 0.1% TFA/H2O: 0.1% TFA/CH3CN gradient followed by conversion to the free base.

Sources & evidence

ORD record
ord-899750f8795945f4ba7065d7861781cd
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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