Ammonia → 4-Bromo-6-methyl-7-oxothieno[2,3-c]pyridine-2-carboxamide

HRID 575753Notes

Reaction equation

[Br:1][C:2]1[C:3]2[CH:12]=[C:11]([C:13]([O:15]C)=O)[S:10][C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[NH3:17]>CO>[Br:1][C:2]1[C:3]2[CH:12]=[C:11]([C:13]([NH2:17])=[O:15])[S:10][C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Using a sealed tube, a solution of methyl 4-bromo-6-methyl-7-oxothieno[2,3-c]pyridine-2-carboxylate (250 mg, 65 mmol) in MeOH (6 mL) stirred at rt was treated with 2N NH3 in methanol (8 ml). The sealed tube was heated to 45° C. for 60 h. After cooling to 0° C., the resulting suspension was filtered; the filter cake was washed with cooled (0° C.) MeOH (3 mL) and isopropyl ether (3 mL) to afford the title compound (215 mg, 95%) as a white solid. LCMS (M+H)+=288.

Workup

temperatureAfter cooling to 0° C.
filtrationthe resulting suspension was filtered
washthe filter cake was washed
temperaturewith cooled (0° C.) MeOH (3 mL) and isopropyl ether (3 mL)

Sources & evidence

ORD record: ord-e526f393bd7e4b58b3c8f33aef4ca7a4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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