Water → HCID 57625526, compound

HRID 2390438Notes

Reaction equation

HRID 2390438 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:19]=[CH:18][C:17](N2C=CC=CC2=O)=[CH:16][CH:15]=1.[C:29]([O-:32])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([N:9]2[CH:5]=[CH:4][C:3]([C:17]3[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:27])[F:28])=[CH:19][CH:18]=3)=[CH:2][C:29]2=[O:32])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 949565-Fluoro-2-nitrotolueneHCID 86628992HCID 86628992, compound

Product 1

HCID 57625526HCID 57625526, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-fluoro-2-nitrotoluene (0.27 g, 2.25 mmol) in DMF (4.0 mL) was added 4-(4-(trifluoromethyl)phenyl-pyridin-2(1H)-one (0.45 g, 1.87 mmol) and Cs2CO3 (0.67 g, 2.1 mmol), and the reaction was heated to 85° C. for 18 h. The reaction mixture was cooled, H2O (20 mL) was added, and the mixture was stirred for 20 min. The resulting solids were collected by filtration and washed with H2O (10 mL). Flash chromatography (silica gel, hexanes/EtOAc, 10:1 to 3:1) yielded the title compound (0.45 g, 65%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.33 (d, J=5.4 Hz, 1H), 8.12-7.89 (m, 5H), 7.65-7.60 (m, 2H), 7.33-7.22 (m, 2H), 2.55 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with H2O (10 mL)

Sources & evidence

ORD record
ord-43e869bbf4b3442eadbc931b256e1332
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

Loading…