Cesium carbonate → HCID 58015560, compound

HRID 422085Notes

Reaction equation

HRID 422085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.F[C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23]([CH3:25])[CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:19]4[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23]([CH3:25])[CH:24]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 949565-Fluoro-2-nitrotolueneHCID 58015550HCID 58015550, compound

Product 1

HCID 58015560HCID 58015560, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(3-chlorophenyl)-5H-furo[3,2-c]pyridine-4-one (1.00 g, 4.08 mmol) in DMF (9.46 mL) was added 5-fluoro-2-nitrotoluene (0.57 mL, 4.7 mmol) and Cs2CO3 (1.32 g, 4.08 mmol). After stirring at 120° C. for 48 h, the reaction mixture was cooled and the solids were collected by filtration. The solids were washed with EtOAc (300 ml) to yield the title compound (1.22 g, 78%) as a golden yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 8.14 (d, J=8.6 Hz, 1H), 7.97 (t, J=17 Hz, 1H), 7.86 (d, J=6.9 Hz, 1H), 7.74 (s, 1H), 7.73 (d, J=7.0 Hz, 1H), 7.68 (d, J=2 Hz, 1H), 7.60 (dd, J=8.0, 2.2 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.46-7.44 (m, 1H), 6.97 (d, J=7.5 Hz, 1H), 2.58 (s, 3H).

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationthe solids were collected by filtration
  3. washThe solids were washed with EtOAc (300 ml)

Sources & evidence

ORD record
ord-c5ea812564bc4be9bd7007378a15ffac
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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