Hydrochloric Acid → HCID 58404774, compound

HRID 1253559Notes

Reaction equation

HRID 1253559 reaction equation
CO[CH:3](OC)[CH2:4]Br.Cl.C(=O)(O)[O-].[Na+].[CH2:14]([O:21][C:22]1[N:27]=[C:26]([NH2:28])[CH:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.O1CCOCC1.C(OCC)(=O)C>[CH2:14]([O:21][C:22]1[N:27]2[CH:3]=[CH:4][N:28]=[C:26]2[CH:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 67204571HCID 67204571, compound

Product 1

HCID 58404774HCID 58404774, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of bromoacetaldehyde dimethyl acetal (0.16 mL, 1.38 mmol) in water (2 mL) was added hydrochloric acid (0.046 mL, 0.276 mmol). After stirring at room temperature for 2 hours, the reaction was heated to 80° C. for 40 mins to give a clear solution. The reaction was cooled down to room temperature, and sodium bicarbonate (147 mg, 1.75 mmol) was added, followed by a solution of 6-(benzyloxy)-4-phenylpyridin-2-amine (254 mg, 0.919 mmol) in 1,4-dioxane (2 mL). The reaction was stirred overnight at ambient temperature, then diluted with ethyl acetate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to give 5-(benzyloxy)-7-phenylimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C20H17N2O [M+H]+, 301.1; found 301.0.

Workup

  1. temperaturethe reaction was heated to 80° C. for 40 mins
  2. customto give a clear solution
  3. temperatureThe reaction was cooled down to room temperature
  4. stirringThe reaction was stirred overnight at ambient temperature
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-6de9f7fe389d42a09acbd4e861dd33c1
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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