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

HRID 483588Notes

Reaction equation

HRID 483588 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-8a23fea0c5a7436a97916a1d9a91467e
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Reaction notes

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