Sodium hydride → HCID 22504428, compound

HRID 1432285Notes

Reaction equation

HRID 1432285 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][CH2:10][OH:11])=[N:6][C:5]([S:12][CH3:13])=[CH:4][N:3]=1.[H-].[Na+].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:1]2[C:2]3=[N:3][CH:4]=[C:5]([S:12][CH3:13])[N:6]=[C:7]3[CH:8]=[C:9]2[CH:10]=[O:11])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 22504411HCID 22504411, compound

Product 1

HCID 22504428HCID 22504428, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 34 (5) (10 mg) in N,N-dimethylformamide (0.5 ml), 60% sodium hydride (3 mg) was added at 0° C. and the mixture was stirred for 20 minutes. To the resulting mixture was added dropwise 4-fluorobenzyl bromide (15 mg) and the mixture was stirred at 15 to 30° C. for 30 minutes. The reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with chloroform, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=5:1) to obtain 15 mg (99.6%) of the desired product as an orange powder.

Workup

  1. stirringthe mixture was stirred at 15 to 30° C. for 30 minutes
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-9a524bbb59154315ac3ea19863162007
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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