Diphenyl sulfide → HCID 178510919, compound

HRID 1875158Notes

Reaction equation

HRID 1875158 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][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](/[CH:25]=[CH:26]/[C:27]#[N:28])[CH:22]=[C:21]([Cl:29])[CH:20]=2)[C:12]=1[F:30])=[O:8].C1(SC2C=CC=CC=2)C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[N:3]=[CH:4][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]([CH2:25][CH2:26][C:27]#[N:28])[CH:22]=[C:21]([Cl:29])[CH:20]=2)[C:12]=1[F:30])=[O:8]

Participants

6

Reactant 2

HCID 8766Diphenyl sulfideHCID 178510917HCID 178510917, compound

Product 1

HCID 178510919HCID 178510919, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-N-{[4-chloro-3-({3-chloro-5-[(E)-2-cyanoethenyl]phenyl}oxy)-2-fluorophenyl]methyl}-1H-imidazole-5-carboxamide (32 mg, 0.069 mmol), diphenylsulfide (1.145 μl, 6.87 μmol) and Pd/C (7.31 mg, 6.87 μmol) in methanol (5 ml) and ethyl acetate (5 ml) was stirred under hydrogen gas (45 psi pressure) overnight. The palladium was filtered off, the solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-[(4-chloro-3-{[3-chloro-5-(2-cyanoethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (22 mg, 0.047 mmol, 69% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.69 (s, 1H), 7.15-7.40 (m, 2H), 7.04 (s, 1H), 6.77 (s, 1H), 6.73 (s, 1H), 4.61 (s, 2H), 2.87 (t, 2H), 2.69 (t, 2H). LC-MS (ES+) m/z 467.02, [M+H].

Workup

  1. filtrationThe palladium was filtered off
  2. customthe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-543ce382fe544bef8f36b16250068683
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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