2,6-Diacetylpyridine → HCID 12143086, compound

HRID 1293497Notes

Reaction equation

HRID 1293497 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:15]=1[NH2:16]>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:15]=1[N:16]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:16][C:15]2[C:14]([F:13])=[CH:20][CH:19]=[CH:18][C:17]=2[F:21])[CH3:11])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 707902,6-DiacetylpyridineHCID 796472,6-Difluoroaniline

Product 1

HCID 12143086HCID 12143086, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Diacetylpyridine (1.76 g, 10.8 mmol) and 2,6-difluoroaniline (2.94 g, 22.8 mmol) were dissolved in 50 ml of toluene. To this solution, 4 Å molecular sieves were added. After standing for 3 days, with addition of more 4 Å molecular sieves the mixture was filtered. The solvent was removed in vacuo. The residue was crystallised from ethanol. Yield of 4: 1 g (24%). 1H-NMR (CDCl3) δ 8.44 (d, 2H, Py-Hm), 7.90 (t, 1H, Py-Hp), 7.05 (m, 2H, ArH) 6.96 (m, 4H, ArH), 2.44 (s, 6H, Me). 19F-NMR (CDCl3) δ −123.6.

Workup

  1. additionTo this solution, 4 Å molecular sieves were added
  2. additionAfter standing for 3 days, with addition of more 4 Å molecular sieves the mixture
  3. filtrationwas filtered
  4. customThe solvent was removed in vacuo
  5. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-166ac7edfd384d3e8581884cf013f5d0
Source dataset
uspto-grants-2007_07
Patent number
US07238764B2

Reaction notes

Loading…