Methanol → HCID 22285044, compound

HRID 1061875Notes

Reaction equation

HRID 1061875 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([C:19]3[N:20]=[CH:21][N:22]([C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:23]=3)=[O:18])[CH:13]=2)[C:8]=1[CH3:43])(=O)=O.C(N(CC)CC)C.[CH3:53][OH:54].CN([CH:58]=[O:59])C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:43][C:8]1[C:9]2[C:10](=[CH:11][C:12]([C:17]([C:19]3[N:20]=[CH:21][N:22]([C:24]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:23]=3)=[O:18])=[CH:13][CH:14]=2)[CH:15]=[CH:16][C:7]=1[C:53]([O:59][CH3:58])=[O:54]

Participants

8

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 86759896HCID 86759896, compound

Product 1

HCID 22285044HCID 22285044, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-methyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthyl trifluoromethanesulfonate (26.8 g), triethylamine (15.7 mL), methanol (50 mL), palladium acetate (0.61 g), 1,1′-bis(diphenylphosphino)ferrocene (1.50 g) and DMF (150 mL) was stirred under a carbon monooxide atmosphere with heating at 70° C. for 16 hrs. The reaction mixture was cooled and diluted with water (1.6 L). The precipitate was collected by filtration and purified by column chromatography (carrier: silica gel, developing solvent: ethyl acetate). The obtained crystal was washed with diisopropyl ether and dried to give the title compound (20.9 g) as-colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe precipitate was collected by filtration
  3. custompurified by column chromatography (carrier: silica gel, developing solvent: ethyl acetate)
  4. washThe obtained crystal was washed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-3d261525736341e5aad33cf064bbb517
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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