Pyridine → HCID 44517800, compound

HRID 1951578Notes

Reaction equation

HRID 1951578 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[O:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33]>ClCCl>[Cl:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([C:9]2[O:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[CH:21][CH:20]=1)=[O:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 57465371HCID 57465371, compound

Product 1

HCID 44517800HCID 44517800, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of 4-(4-phenyl-5-(trifluoromethyl)oxazol-2-yl)benzenamine (178 mg, 585 μmol) and pyridine (473 μl, 5850 μmol) in 5 mL dichloromethane at room temperature was added 2-chlorobenzoyl chloride (78.0 μl, 614 μmol) all at once by pipet. After one hour the reaction was concentrated under reduced pressure then taken up in 25 mL dichloromethane and washed with 25 mL saturated aqueous sodium bicarbonate solution. The organic separation was stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow oil. The product was isolated by chromatography on silica gel, eluting with 15-40% ethyl acetate in hexane, to yield a colorless foamy solid (213 mg, 82%). ESI+ m/z=443.0 [MH]+.

Workup

  1. concentrationAfter one hour the reaction was concentrated under reduced pressure
  2. washwashed with 25 mL saturated aqueous sodium bicarbonate solution
  3. customThe organic separation
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford a yellow oil
  7. customThe product was isolated by chromatography on silica gel
  8. washeluting with 15-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-951f787d31584fdd90df7e1fee19f769
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

Loading…