Phenacyl bromide → Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylate

HRID 872243Notes

Reaction equation

HRID 872243 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([Br:12])=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>C(O)C>[Br:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]2[N:11]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:1]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 25307230Methyl 2-amino-5-bromoisonicotinate

Product 1

HCID 67041599Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylateYield 55.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 40 mL pressure rated scintillation vial was charged with methyl 2-amino-5-bromoisonicotinate (500 mg, 2.16 mmol) and 2-bromo-1-phenylethanone (474 mg, 2.38 mmol). The mixture was partially dissolved in ethanol (10.8 mL) and the reaction vessel was placed in a reaction block preheated to 100° C. The reaction mixture was let stir overnight. After heating for 18 hours, LCMS showed complete conversion of the starting material to a major peak with the desired mass (m/z=332 [M+H]+). The mixture was allowed to come to ambient temperature. After several hours a red precipitate had formed and was filtered. The solid was dried in open air overnight. Methyl 6-bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylate (400 mg, 1.208 mmol, 55.8% yield) was collected as a red solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.12 (1H, s), 8.58 (1H, s), 8.18 (1H, s), 8.01 (2H, dd, J=8.28, 1.25 Hz), 7.53 (2H, t, J=7.53 Hz), 7.41-7.47 (1H, m), 3.93 (3H, s). Mass found 332 [M+H]+.

Workup

  1. custompreheated to 100° C
  2. temperatureAfter heating for 18 hours
  3. customto come to ambient temperature
  4. customAfter several hours a red precipitate had formed
  5. filtrationwas filtered
  6. customThe solid was dried in open air overnight

Sources & evidence

ORD record
ord-4962f8c953f744f4bd44480901a919d4
Source dataset
uspto-grants-2015_03
Patent number
US08975276B2

Reaction notes

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