HCID 59191409, compound → HCID 59191408, compound

HRID 1023924Notes

Reaction equation

HRID 1023924 reaction equation
CC1C=CC(S(O[CH:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[N:25]=3)=[C:19]([O:31][CH3:32])[CH:18]=2)[C:13]([F:16])([F:15])[F:14])(=O)=O)=CC=1.[H][H]>C(O)C.[Pd]>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([CH2:12][C:13]([F:16])([F:14])[F:15])=[CH:18][C:19]=2[O:31][CH3:32])[N:25]=1

Participants

5

Reactant 2

HCID 59191409HCID 59191409, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59191408HCID 59191408, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2,2,2-trifluoro-1-{4-[(6-fluoropyridin-2-yl)oxy]-3-methoxyphenyl}ethyl 4-methylbenzenesulfonate (0.2 mmol; 96 mg) in ethanol (3 ml) containing a catalytic amount of Pd/C (10% wet; 0.014 mmol; 30 mg) was stirred for 16 h at rt under 2.5 atm of hydrogen. Purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70) afforded the title compound (48 mg; 0.16 mmol; 80%).

Workup

  1. customPurification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-21cfff790332420c9b898bf2f4eea753
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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