3-Iodo-8-methoxy-2-phenyl-pyrano[2,3-c]pyridin-4-one → 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

HRID 1037254Notes

Reaction equation

[I:1][C:2]1[C:3](=[O:20])[C:4]2[C:5]([O:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:6]([O:10]C)[N:7]=[CH:8][CH:9]=2>Br.CC(O)=O>[I:1][C:2]1[C:3](=[O:20])[C:4]2[CH:9]=[CH:8][NH:7][C:6](=[O:10])[C:5]=2[O:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 3-iodo-8-methoxy-2-phenyl-pyrano[2,3-c]pyridin-4-one (0.30 g, 0.791 mmol) in 33% hydrogen bromide solution in AcOH (3 mL) was heated in a microwave oven at 60° C. for 40 minutes. After coiling to RT, the reaction mixture was added to rapidly stirred ice-cold water (30 mL). After stirring for 10 min, the solid was collected by filtration, washed with water and dried in vacuo at 50° C. to give the title compound (0.28 g, 97%) as a white solid. LCMS (Method A): RT=3.74 min, [M+H]+=366.

Workup

customAfter coiling to RT
filtrationthe solid was collected by filtration
washwashed with water
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-11d1e3311c1446ce96ddb5cae8cb42c2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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