Chloroform → 4-(2-(4-fluoro-N-benzoylamino)benzoyl)pyridine

HRID 395951

Reaction equation

HRID 395951 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C.C(Cl)(Cl)Cl>O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=2[C:14]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[O:15])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 14005182(2-Aminophenyl)(pyridin-4-yl)methanone

Product 1

HCID 181752494-(2-(4-fluoro-N-benzoylamino)benzoyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluorobenzoyl chloride (78.0 mg, 0.55 mmol) was added to 4-(2-aminobenzoyl)pyridine (12) (100 mg, 0.50 mmol), triethylamine (0.35 mL, 2.52 mL), and chloroform (5.0 mL) at 23° C. under argon. After 24 h at 23° C., the reaction was poured into water (50 mL), extracted with ethyl acetate (3×50 mL), and dried (MgSO4). After concentration in vacuo, the residue was purified by flash chromatography (ethyl acetate:methylene chloride 1:1) to afford 4-(2-(4-fluoro-N-benzoylamino)benzoyl)pyridine (14): Mass Spectrum (CI) 321 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (ethyl acetate:methylene chloride 1:1)

Sources & evidence

ORD record
ord-63470f7b151e47ca901cfe17538a4025
Source dataset
uspto-grants-2003_08
Patent number
US06605634B2

Linked notes

Loading…