1,4-Dioxane → Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

HRID 1253568Notes

Reaction equation

HRID 1253568 reaction equation
I[C:2]1[N:6]2[C:7]([O:17][CH3:18])=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[S:30][CH:31]=2)O1.C(=O)(O)[O-].[Na+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:18][O:17][C:7]1[N:6]2[C:2]([C:27]3[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[S:30][CH:31]=3)=[CH:3][N:4]=[C:5]2[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylateHCID 584048583-Iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine

Product 1

HCID 58404681Methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3-iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine (166 mg, 0.474 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (254 mg, 0.948 mmol), tetrakis(triphenylphosphine)palladium (0) (55.0 mg, 0.047 mmol), and sodium bicarbonate (150 mg, 1.42 mmol) were added to a dry flask. Dioxane (5 ml) and water (0.5 ml) were added and the reaction mixture was sparged with argon for 3 minutes. The reaction mixture was heated to 90° C. After 6 h the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/dichloromethane gradient) to give methyl 4-(5-methoxy-7-phenylimidazo[1,2-a]pyridin-3-yl)thiophene-2-carboxylate. LRMS (ESI) calculated for C20H17N2O3S [M+H]+, 365.1 found 365.0.

Workup

  1. customthe reaction mixture was sparged with argon for 3 minutes
  2. temperatureAfter 6 h the reaction mixture was cooled to ambient temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate/dichloromethane gradient)

Sources & evidence

ORD record
ord-7b2be4d79f0e4c4fbb6c612050161090
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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