HCID 86709376, compound → HCID 67275859, compound

HRID 2172199Notes

Reaction equation

HRID 2172199 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[F:32][C:29]([F:30])([F:31])[O:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH:18]2[CH2:17][CH2:16][N:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=3)[CH2:20][CH2:19]2)=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 86709376HCID 86709376, compound

Product 1

HCID 67275859HCID 67275859, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5′-Benzyloxy-4-(4-trifluoromethoxyphenoxy)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (0.93 g) and 10% palladium on carbon (93 mg) were added to ethanol (9.3 ml), and the mixture was stirred at room temperature under a hydrogen atmosphere (atmospheric pressure) for 1 hour. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4). The result was concentrated to dryness under reduced pressure to afford the title compound as a pale yellow powder (0.55 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4)
  4. concentrationThe result was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-41eb99d0a3134bf6ba27a00574f528cc
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…