Benzyl Bromide → HCID 86698188, compound

HRID 623942Notes

Reaction equation

HRID 623942 reaction equation
CN(C)C(=O)C.[Br:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[NH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][N:18]=2)=[CH:10][CH:9]=1.C(N(C(C)C)CC)(C)C.[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[Br:7][C:8]1[N:13]=[CH:12][C:11]([C:14]2[NH:15][C:16]([C:19]([O:21][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:20])=[CH:17][N:18]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 86698187HCID 86698187, compound

Product 1

HCID 86698188HCID 86698188, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylacetamide solution containing 2-(6-bromopyridin-3-yl)-1H-imidazol-5-carboxylic acid (4.99 g) and diisopropylethylamine (4.21 mL) was added benzyl bromide (3.81 g) under ice-cooling, after stirring the mixture for 5 minutes, the temperature of the mixture was raised to room temperature and the mixture was stirred overnight. Water was added to the reaction mixture under ice-cooling, and the precipitated solid was collected by filtration, washed with water and n-hexane, and dried to obtain benzyl 2-(6-bromopyridin-3-yl)-1H-imidazol-5-carboxylate (6.01 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight
  3. temperaturecooling
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water and n-hexane
  6. customdried

Sources & evidence

ORD record
ord-162fa59ea51c466f949a3a9b08486615
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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