Propargyl bromide → HCID 19436746, compound

HRID 260966Notes

Reaction equation

HRID 260966 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:22]([F:23])=[CH:21][C:15]3[NH:16][C:17](=[O:20])[CH2:18][O:19][C:14]=3[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].[CH2:24](Br)[C:25]#[CH:26]>CS(C)=O.O>[Cl:1][C:2]1[C:3]([C:12]2[C:22]([F:23])=[CH:21][C:15]3[N:16]([CH2:26][C:25]#[CH:24])[C:17](=[O:20])[CH2:18][O:19][C:14]=3[CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10]

Participants

5

Reactant 2

HCID 7842Propargyl bromideHCID 19436759HCID 19436759, compound

Product 1

HCID 19436746HCID 19436746, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

At 25° C., 2.7 g (7.7 mmole) the product of step A, 1.1 g (8.0 mmole) KCO3 and 0.9 mL (8.0 mmole) 80% propargyl bromide were slurried in 25 mL DMSO. The mixture was stirred at 45° C. for 16 hours. The mixture was cooled, diluted with 100 mL cold water and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4 and stripped in vacuo. The residue was purified chromatographically using methylene chloride as the eluent to give 2.7 g (90%) of 7-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-6-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one as a white solid, mp 184° C.

Workup

  1. customAt 25° C.
  2. temperatureThe mixture was cooled
  3. extractionextracted four times with ethyl acetate
  4. washThe ethyl acetate extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe residue was purified chromatographically using methylene chloride as the eluent

Sources & evidence

ORD record
ord-ef16d26d8bd74363b822b1612bc152b4
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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