Ethanol → 8-Benzyloxy-6-ethoxycarbonyl-2,3-dimethylimidazo[1,2-a]pyridine

HRID 895603Notes

Reaction equation

HRID 895603 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([C:34]2[CH:39]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:48].[CH2:49]([OH:51])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:12]=[C:13]([C:49]([O:51][CH2:39][CH3:34])=[O:48])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 121060818-(Benzyloxy)-6-bromo-2,3-dimethylimidazo[1,2-a]pyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 121060828-Benzyloxy-6-ethoxycarbonyl-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 4 g of 8-benzyloxy-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine, 0.4 g of palladium(II) acetate, 1.33 g of triphenylphosphine, 10 ml of triethylamine and 50 ml of ethanol is heated for 16 h in a carbon monoxide atmosphere in an autoclave (5 bar), the volatile portions are stripped off in vacuo and the residue is chromatographed on silica gel (eluent: ethyl acetate). 2.4 g of the title compound of melting point 140-1° C. (diethyl ether) are obtained.

Workup

  1. customthe residue is chromatographed on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-74985d35eaf442e4b7d8e83b4b38fe17
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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