Sodium Carbonate → 5-Methoxy-7-phenylimidazo[1,2-a]pyridine

HRID 1253565Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[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>[CH3:9][O:8][C:6]1[N:5]2[CH:10]=[CH:11][N:12]=[C:4]2[CH:3]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

7-iodo-5-methoxyimidazo[1,2-a]pyridine (539 mg, 1.97 mmol), phenylboronic acid (719 mg, 5.90 mmol), tetrakis(triphenylphosphine)palladium (0) (227 mg, 0.197 mmol), and sodium carbonate (625 mg, 5.90 mmol) were added to a dry flask. Dioxane (18 ml) and water (2 ml) were added and the reaction mixture was sparged with argon for 5 minutes. The reaction mixture was heated to 85° C. After 16 h, the reaction mixture was cooled, 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 (methanol/dichloromethane gradient) to give 5-methoxy-7-phenylimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C14H13N2O [M+H]+, 225.1 found 225.0.

Workup

customthe reaction mixture was sparged with argon for 5 minutes
temperaturethe reaction mixture was cooled
additiondiluted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient)

Sources & evidence

ORD record: ord-f882d13039864629b3d4bc94974e84be
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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