4-Fluorobenzyl bromide → HCID 9821271, compound

HRID 1432218Notes

Reaction equation

HRID 1432218 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][C:8]2=[N:9][CH:10]=1)(=[O:4])=[O:3].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.[H-].[Na+]>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=3)[C:8]2=[N:9][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 516892Sodium BicarbonateHCID 15486861HCID 15486861, compound

Product 1

HCID 9821271HCID 9821271, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of the compound obtained in Example 5 (4) (2.3 mg) in N,N-dimethylformamide (0.5 ml), 60% sodium hydride. (0.5 mg) was added at 0° C. and the mixture was stirred at the same temperature for 15 minutes. p-Fluorobenzyl bromide. (2.4 mg) was then added thereto at 0° C. and the mixture was stirred at 15 to 30° C. for 1 hour. The reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with toluene, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (chloroform:methanol=100:1) to obtain 1.7 mg of the desired product as a white powder.

Workup

  1. addition(0.5 mg) was added at 0° C.
  2. addition(2.4 mg) was then added
  3. stirringat 0° C. and the mixture was stirred at 15 to 30° C. for 1 hour
  4. extractionextracted with toluene
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was separated

Sources & evidence

ORD record
ord-e5edba3766d745a1953f9dc846ac0af4
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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