HCID 90409113, compound → HCID 86271758, compound

HRID 2177564Notes

Reaction equation

HRID 2177564 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH:19]=[CH:18][C:17]2[N:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH:21]=[N:22][C:16]=2[CH:15]1[CH3:30])=[O:13]>CCO.[Pd].C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[N:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH:21]=[N:22][C:16]=2[CH:15]1[CH3:30])=[O:13]

Participants

5

Reactant 1

HCID 90409113HCID 90409113, compound

Product 1

HCID 86271758HCID 86271758, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyridin-2-yl)-4-methyl-1H-imidazo[4,5-c]pyridin-5(4H)-yl)methanone (0.80 g, 1.83 mmol) in degassed EtOH (25 mL) was added 10% palladium on carbon (0.20 mg, 0.19 mmol). The reaction was placed under an atmosphere of hydrogen and let stir for 48 h. The reaction was diluted with DCM and filtered through a pad of Celite®. The solvent was concentrated and chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (500 mg, 62%). 1H NMR (500 MHz, CDCl3) δ 8.45-8.30 (m, 1H), 7.94 (dd, J=18.2, 10.7 Hz, 1H), 7.76 (d, J=5.7 Hz, 1H), 7.67-7.43 (m, 3H), 7.43-7.30 (m, 1H), 5.81 (dd, J=13.3, 6.7 Hz, 1H), 5.07 (d, J=5.6 Hz, 1H), 4.52 (d, J=6.7 Hz, 1H), 3.61-3.31 (m, 1H), 3.08-2.69 (m, 1H), 1.63-145 (m, 3H). MS (ESI): mass calculated for C20H15ClF4N4O, 438.08. m/z found 439.1 [M+H]+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-23a7ae9d21fe4dff89c865f7ae89459c
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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