Sodium hydride → HCID 9929964, compound

HRID 1432231Notes

Reaction equation

HRID 1432231 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]3[O:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[NH:11][C:8]2=[N:9][CH:10]=1)(=[O:4])=[O:3].[H-].[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:11]2[C:8]3=[N:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[C:7]3[CH:13]=[C:12]2[C:14]2[O:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 516892Sodium BicarbonateHCID 22504368HCID 22504368, compound2×

Product 1

HCID 9929964HCID 9929964, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 11′ (3) (20,mg) in N,N-dimethylformamide (2 ml), 60% sodium hydride (4.4 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 30 minutes, followed by addition of 4-fluorobenzyl bromide (2.6 mg), and the reaction mixture was stirred for further 30 minutes. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with toluene. The organic layer was washed with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate 1:1) to obtain 18 mg of the desired product as a yellow powder.

Workup

  1. stirringthe reaction mixture was stirred for further 30 minutes
  2. extractionextracted with toluene
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-397e0b20a2b04a2d8ef29b0aa147be0d
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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