2-(6-(4-(Benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazole → HCID 178516382, compound

HRID 1028064Notes

Reaction equation

HRID 1028064 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[N:24]=[C:23]([C:25]4[S:26][CH:27]=[CH:28][N:29]=4)[CH:22]=[CH:21][CH:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CCO.CCOC(C)=O>[S:26]1[CH:27]=[CH:28][N:29]=[C:25]1[C:23]1[N:24]=[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:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 583875912-(6-(4-(Benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazole

Product 1

HCID 178516382HCID 178516382, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 2-(6-(4-(benzyloxy)quinolin-6-yl)pyridin-2-yl)thiazole (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-(thiazol-2-yl)pyridin-2-yl)quinolin-4-ol (88%). LCMS (m/z): 305.9 (MH+); LC Rt=2.57 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-28ce33e59c8648848bbab5cab51c0145
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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