Imidazo(1,2-a)pyridine → HCID 19925050, compound

HRID 1461931Notes

Reaction equation

HRID 1461931 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[N:34]1[CH:35]=[CH:36][N:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=12>C(#N)C>[Br-:1].[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C:5]2[CH:4]=[C:3]([CH2:2][N+:34]3[CH:35]=[C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][N:37]4[CH:38]=3)[CH:8]=[CH:7][CH:6]=2)=[O:33])=[CH:13][CH:14]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 78960Imidazo(1,2-a)pyridineHCID 10052253N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)-benzeneacetamide

Product 1

HCID 19925050HCID 19925050, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.5 g of N-[3-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 1.03 g of imidazo[1,2-a]pyridine in 25 ml of acetonitrile is refluxed under argon for 3.5 hours. The solvent is evaporated and the residue stirred with ether and collected by centrifugation. The solid is washed several times with ether and vacuum dried to give 1.5 g of the desired product as a white powder, m.p. 133°-135° C.

Workup

  1. temperatureis refluxed under argon for 3.5 hours
  2. customThe solvent is evaporated
  3. customcollected by centrifugation
  4. washThe solid is washed several times with ether and vacuum
  5. customdried

Sources & evidence

ORD record
ord-628af038389d48b9b131233d55788adc
Source dataset
uspto-grants-1991_12
Patent number
US05077409

Reaction notes

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