Sodium hydride → HCID 10712692, compound

HRID 1290161Notes

Reaction equation

HRID 1290161 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[C:8]2[N:9]([CH:13]=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)(=[O:5])[CH3:4].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:19]=1[CH2:20]Br>O>[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:19]=1[CH2:20][N:6]([C:7]1[C:8]2[N:9]([CH:13]=[C:14]([CH3:16])[N:15]=2)[CH:10]=[CH:11][CH:12]=1)[C:3](=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 18923298HCID 18923298, compound

Product 1

HCID 10712692HCID 10712692, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of sodium hydride (60% oil dispersion, 17 mg) was added 8-acetylamino-2-methylimidazo[1,2-a]pyridine (73 mg), and the mixture was stirred for 30 minutes, 2,6-dichlorobenzyl bromide (97 mg) was added thereto, and the mixture was stirred for 1 hour. Water was added thereto, and the mixture was extracted with methylene chloride three times. The combined organic layer was washed with water four times and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized with diethyl ether to give 8-[N-(2,6-dichlorophenyl)methyl-N-acetylamino]-2-methylimidazo[1,2-a]pyridine (85 mg).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with methylene chloride three times
  3. washThe combined organic layer was washed with water four times and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized with diethyl ether

Sources & evidence

ORD record
ord-7d0a50c166c84bf49fcd3cd798593b2d
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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