(R)-1-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol → (R)-2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanol

HRID 1499245Notes

Reaction equation

HRID 1499245 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4].BrC1C=CC([C@@H](O)C(F)(F)F)=C(N2C=CC(C)=N2)C=1>[Ir]>[F:22][C:2]([F:1])([F:21])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:4]

Participants

4

Reactant 2

HCID 117942080(R)-1-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol2×HCID 1179521742,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanone

Product 1

HCID 117953061(R)-2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 23924IridiumCatalyst

Procedure

Chiral reduction of 2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)ethanone using the Iridium complex-catalyzed hydrogenation as described for Intermediate 1, (R)-1-(4-bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol, provided (R)-2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)ethanol as a white solid.

Sources & evidence

ORD record
ord-2f7721a8c2a540a49e7613d6df29ad7a
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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