HCID 86608616, compound → HCID 59813615, compound

HRID 1925299Notes

Reaction equation

HRID 1925299 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1>CCOC(C)=O.CO.[Pd]>[N:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[CH:23]=2)=[O:20])=[CH:14][CH:13]=[CH:12]3)=[N:7][CH:2]=1

Participants

5

Reactant 1

HCID 86608616HCID 86608616, compound

Product 1

HCID 59813615HCID 59813615, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(2-chloropyrimidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1-naphthamide (0.075 g, 0.17 mmol) in EtOAc (3 mL) and methanol (0.5 mL) was added 10% Pd/C (20 mg). The flask was capped with a septum, and H2 gas was introduced through a balloon/needle. Positive H2 pressure was continued as the reaction was stirred vigorously overnight at RT. The reaction was filtered through Celite, concentrated, and purified by chromatography on silica to afford the desired product as a white solid. MS (ESI, pos. ion) m/z: 410.1 (M+1). Mass Calc'd for C22H14F3N3O2: 409.36.

Workup

  1. customThe flask was capped with a septum, and H2 gas
  2. additionwas introduced through a balloon/needle
  3. filtrationThe reaction was filtered through Celite
  4. concentrationconcentrated
  5. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-7e5e747c2c6847b29ca2f5e41b68de0f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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