Water → HCID 18519629, compound

HRID 1368028Notes

Reaction equation

HRID 1368028 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([Cl:19])=[C:14]([OH:20])[C:13]=2[NH2:21])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].Br[CH:23]([CH3:29])[C:24](OCC)=[O:25].C(=O)([O-])[O-].O>C(#N)C>[Cl:1][C:2]1[C:3]([C:12]2[C:13]3[NH:21][C:24](=[O:25])[CH:23]([CH3:29])[O:20][C:14]=3[C:15]([Cl:19])=[CH:16][C:17]=2[F:18])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9]

Participants

6

Reactant 4

HCID 962WaterHCID 19660Carbonate IonHCID 79040Ethyl 2-bromopropionateHCID 18519625HCID 18519625, compound

Product 1

HCID 18519629HCID 18519629, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Step 3 A mixture of 4-chloro-3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole (0.88 g), ethyl 2-bromopropionate (0.70 g) and potassiun carbonate (0.711 g) in acetonitrile (30 ml) was stirred overnight at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine (×3) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the oily product was subjected to silica gel chromatography eluted with ethyl acetate and hexane (1:4) to afford 4-chloro-3-(8-chloro-6-fluoro-2-methyl-2H-1,4-benzoxazine-3-one-5-yl)-5-difluoromethoxy-1-methyl-1H-pyrazole (0.054 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine (×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washeluted with ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-97091d261ab84c56a4b92a9a4c3072e1
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

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