Pyridine → HCID 86720244, compound

HRID 2166975Notes

Reaction equation

HRID 2166975 reaction equation
[Br:1][C:2]1[C:7]2[NH:8][C:9](=O)[O:10][C:11](=[O:12])[C:6]=2[CH:5]=[C:4]([Cl:14])[CH:3]=1.[Cl:15][C:16]1[C:17]([N:22]2[C:26](C(Cl)=O)=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1.N1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([C:26]3[N:22]([C:17]4[C:16]([Cl:15])=[CH:21][CH:20]=[CH:19][N:18]=4)[N:23]=[C:24]([C:30]([F:31])([F:32])[F:33])[CH:25]=3)[O:10][C:11](=[O:12])[C:6]=2[CH:5]=[C:4]([Cl:14])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 28332426HCID 28332426, compound

Product 1

HCID 86720244HCID 86720244, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 8-Bromo-6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (5.0 g, 18.1 mmol) in acetonitrile (10 mL) was added a solution of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride (6.45 g, 20.8 mmol) in acetonitrile (8 mL). After stirring for 5 min pyridine (10.4 mL) was added dropwise. The reaction was stirred for a further 30 min at room temperature, then heated to 100° C. for 4 h and stirred for a further 16 h at room temperature. The reaction was then cooled in an ice-bath and the resulting white solid filtered and washed with cold acetonitrile to obtain the title compound (5.88 g, 64%).

Workup

  1. additionwas added dropwise
  2. temperatureheated to 100° C. for 4 h
  3. stirringstirred for a further 16 h at room temperature
  4. temperatureThe reaction was then cooled in an ice-bath
  5. filtrationthe resulting white solid filtered
  6. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-dbabea4b005d457bafaf2f00dbe46a36
Source dataset
uspto-grants-2015_06
Patent number
US09044016B2

Reaction notes

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