Pyridine → 8-bromo-2-(3-(trifluoromethyl)phenyl)-4H-pyrido[4,3-d][1,3]oxazin-4-one

HRID 520470Notes

Reaction equation

HRID 520470 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[Br:11].N1C=CC=CC=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=O>O>[Br:11][C:3]1[C:2]2[N:1]=[C:23]([C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=3)[O:9][C:8](=[O:10])[C:7]=2[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 215304944-Amino-5-bromopyridine-3-carboxylic acid

Product 1

HCID 585528348-bromo-2-(3-(trifluoromethyl)phenyl)-4H-pyrido[4,3-d][1,3]oxazin-4-oneYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-4-aminonicotinic acid 46 (10.5 g, 48.4 mmol) and pyridine (60 mL) was heated at 60° C. until homogeneous. 3-(trifluoromethyl)benzoyl chloride 2 (8.0 mL, 53.0 mmol) was added and stirring continued for 2 h. H2O (200 mL) was added and the mixture cooled to 0° C. The resulting yellow precipitate was collected by filtration, rinsed with H2O (100 mL) then pentane (100 mL), and dried under vacuum to give the 47 (8.50 g, 47% yield).

Workup

  1. temperaturethe mixture cooled to 0° C
  2. filtrationThe resulting yellow precipitate was collected by filtration
  3. washrinsed with H2O (100 mL)
  4. dry with materialpentane (100 mL), and dried under vacuum

Sources & evidence

ORD record
ord-6846cbec9ed7428085c7c2000640d7f0
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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