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

HRID 2227080Notes

Reaction equation

HRID 2227080 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-b69d95fb58764dca8556431735fdd0b8
Source dataset
uspto-grants-1994_09
Patent number
US05350759

Reaction notes

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