HCID 71114189, compound → HCID 71114184, compound

HRID 710189Notes

Reaction equation

HRID 710189 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:13][N:12]=3)=[CH:5][CH:4]=1>CO.[Pd]>[F:31][C:2]([F:1])([F:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]2)=[CH:13][N:12]=3)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 71114189HCID 71114189, compound

Product 1

HCID 71114184HCID 71114184, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl 4-{2-[4-(trifluoromethyl)phenyl]oxazolo[5,4-b]pyridin-6-yl}-5,6-dihydropyridine-1(2H)-carboxylate (170 mg, 0.38 mmol) was dissolved in methanol (10 ml) and added Pd/C (5%) (283 mg). This mixture was stirred under H2 pressure (6.5 kg) for 12 h. Combined methanol fractions were evaporated on rotavapour to obtain the crude. Crude was purified on combiflash using a gradient mixture of EtOAc and Petether (1:9) as eluent to afford the titled compound (35 mg) as a white solid. M. P.: 184-188° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.40 (d, J 8.1, 2H), 8.27 (d, J 2, 1H), 7.93 (d, J 2, 1H), 7.81 (d, J 8.3, 2H), 4.31 (d, J 13.5, 2H), 2.91-2.81 (m, 3H), 1.91 (d, J 12.9, 2H), 1.78-1.62 (m, 2H), 1.50 (s, 9H).

Workup

  1. customCombined methanol fractions were evaporated on rotavapour
  2. customto obtain the crude
  3. customCrude was purified on combiflash
  4. additiona gradient mixture of EtOAc and Petether (1:9) as eluent

Sources & evidence

ORD record
ord-d3f81cb8beef4a63813f038ea1f0fb77
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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