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

HRID 481026Notes

Reaction equation

HRID 481026 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.[C:21]([O-:24])(=[O:23])C.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:26]=1.[C]=O>[Pd].C(O)C.C(N(CC)CC)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:21]([O:24][CH2:25][CH3:26])=[O:23])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 175AcetateHCID 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 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4 g of 8-benzyloxy-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine, 0.4 g of palladium( acetate, 1.33 g of triphenylphosphine, 10 ml of triethylamine and 50 ml of ethanol is heated for 16 h) a carbon monoxide atmosphere in an autoclave (5 bar), the volatile portions are stripped off in vaco and the residue is chromatographed on silica gel (eluent: ethyl acetate). 2.4 g of the title compound 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-67de1b14ab62478188cfb7eee16c6ff0
Source dataset
uspto-grants-2003_11
Patent number
US06653477B2

Reaction notes

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