Diphenyl sulfide → HCID 178436596, compound

HRID 1875125Notes

Reaction equation

HRID 1875125 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:30])[NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([CH:27]=[CH2:28])[N:20]=2)[C:12]=1[F:29])=[O:8].C1(SC2C=CC=CC=2)C=CC=CC=1>[Pd].CO.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:30])[NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([CH2:27][CH3:28])[N:20]=2)[C:12]=1[F:29])=[O:8]

Participants

6

Reactant 2

HCID 8766Diphenyl sulfideHCID 178436595HCID 178436595, compound

Product 1

HCID 178436596HCID 178436596, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-N-({4-chloro-3-[(4-cyano-6-ethenyl-2-pyridinyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (53 mg, 0.119 mmol), diphenylsulfide (1.979 μl, 0.012 mmol) and palladium on carbon (12.64 mg, 0.012 mmol, 10%) in MeOH (8.0 ml) and ethyl acetate (8.00 ml) was reacted under H2 (40 psi) overnight. The reaction mixture was filtered through a pad of celite and concentrated to dryness. The residue was purified by flash chromatography on silica gel eluted with 0-5% 2M NH3 solution of MeOH in CH2Cl2 to give the title compound as a white solid (43 mg, 81%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.82 (1H, br. s.) 7.17-7.24 (2H, m) 7.09 (2H, d, J=5.4 Hz) 4.68 (2H, d, J=6.0 Hz) 2.61 (2H, q, J=7.5 Hz) 2.39 (3H, s) 1.07 (3H, t). LCMS: m/z 448 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by flash chromatography on silica gel
  4. washeluted with 0-5% 2M NH3 solution of MeOH in CH2Cl2

Sources & evidence

ORD record
ord-0d3c7bd33c7c4ad4b14e1766cde73cc0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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