HCID 57465377, compound → HCID 57465378, compound

HRID 1951588Notes

Reaction equation

HRID 1951588 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:21]([F:24])([F:23])[F:22])=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[N:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:14]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[O:11][C:12]=2[C:21]([F:24])([F:22])[F:23])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 57465377HCID 57465377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57465378HCID 57465378, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

to a nitrogen purged flask charged with palladium on carbon (0.032 g, 0.30 mmol) and 4-(2-(4-nitrophenyl)-5-(trifluoromethyl)oxazol-4-yl)pyridine (1.015 g, 3.0 mmol) in 40 mL ethyl acetate was introduced hydrogen (0.0061 g, 3.0 mmol) by balloon. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 18 h then purged with nitrogen and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford a yellow solid. The desired product was isolated by chromatography on silica, eluting with 100% ethyl acetate, affording product as a colorless solid (0.52 g, 56%). ESI+ m/z=306.1 [MH]+.

Workup

  1. customthen purged with nitrogen
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford a yellow solid

Sources & evidence

ORD record
ord-9c79edb990d04583a4af7faabad97dc6
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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