Propargyl bromide → HCID 22114860, compound

HRID 1276086Notes

Reaction equation

HRID 1276086 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:21]=[C:20]3[C:15]([N:16]([CH3:23])[CH2:17][C:18](=[O:22])[NH:19]3)=[CH:14][CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:26](Br)[C:27]#[CH:28]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[CH:21]=[C:20]3[C:15]([N:16]([CH3:23])[CH2:17][C:18](=[O:22])[N:19]3[CH2:28][C:27]#[CH:26])=[CH:14][CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 22114850HCID 22114850, compound

Product 1

HCID 22114860HCID 22114860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.0 g of 7-(3-chloro-5-trifluoromethylpyridin-2yl)-1,2,3,4-tetrahydro-4-methylquinoxalin-2-one in 35 ml of dimethylformamide was added dropwise to a suspension of 0.2 g of 80% strength by weight sodium hydride in 35 ml of anhydrous dimethylformamide. After stirring for 15 minutes, 0.73 g of propargyl bromide was added to the reaction mixture. After 18 hours at 23° C., the reaction mixture was poured into 300 ml of ice water and extracted three times with 100 ml of tert-butyl methyl ether each time, after which the combined organic phases were washed twice with 100 ml of water each time, dried over sodium sulfate and concentrated. Purification of the crude product was carried out by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate). Yield: 1.1 g (49%) of colorless crystals; m.p.: 128-129° C.

Workup

  1. waitAfter 18 hours at 23° C.
  2. extractionextracted three times with 100 ml of tert-butyl methyl ether each time
  3. washafter which the combined organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the crude product

Sources & evidence

ORD record
ord-1ab86f6f5ca8411e914050dc8d4726b5
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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