4-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline → HCID 178516381, compound

HRID 1028067Notes

Reaction equation

HRID 1028067 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[N:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CCO.CCOC(C)=O>[F:31][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([F:32])[C:25]=1[C:21]1[N:20]=[C:19]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][CH:10]=[C:9]3[OH:8])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 583875674-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline

Product 1

HCID 178516381HCID 178516381, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 4-(benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline (1.0 equiv.) in 1:1 EtOH/EtOAc, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 72 hours. At this time the mixture was filtered through a pad of celite eluting with EtOAc. The volatiles were removed in vacuo yielding 6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinolin-4-ol (70%). LCMS (m/z): 335.0 (MH+); LC Rt=3.09 min.

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with EtOAc
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-986f4bf35ed94ec2b4a4b18e656bbf22
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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