HCID 25131530, compound → HCID 25131882, compound

HRID 2076941Notes

Reaction equation

HRID 2076941 reaction equation
FC(F)(F)S(O[C:7]1[N:11]([CH2:12][C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]([C@@H:17]2[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19][C@H:18]2[CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]=1[C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1)(=O)=O>[Pd].C(OCC)(=O)C>[CH2:27]([O:26][CH2:25][C@@H:18]1[CH2:19][C:20]([F:23])([F:24])[CH2:21][CH2:22][C@H:17]1[C:9]1[C:8]([C:34]2[CH:35]=[CH:36][C:37]([S:40]([CH3:43])(=[O:41])=[O:42])=[CH:38][CH:39]=2)=[CH:7][N:11]([CH2:12][C:13]([F:15])([F:16])[F:14])[N:10]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 25131530HCID 25131530, compound

Product 1

HCID 25131882HCID 25131882, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{(1R,2R)-2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl trifluoromethanesulfonate (4.54 g, 6.58 mmol) and 10% palladium on charcoal (2.20 g) were stirred together in ethyl acetate (60 mL) under an atmosphere of hydrogen gas at rt for 16 h. Filtration through Celite®, concentration of the filtrate and flash chromatography on silica gel eluting with 45/55 ethyl acetate/hexanes yielded 3-{(1R,2R)-2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole as a colorless, thick syrup.

Workup

  1. filtrationFiltration through Celite®, concentration of the filtrate and flash chromatography on silica gel eluting with 45/55 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-182f244f3eea42dc94006a0bc3357827
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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