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

HRID 1037246Notes

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)=[N:6][C:7]([O:10]C)=[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][C:7](=[O:10])[NH:6][C:5]=2[O:12][C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 3-iodo-7-methoxy-2-phenyl-pyrano[2,3-b]pyridin-4-one (0.25 g, 0.66 mmol) in 33% hydrogen bromide solution in AcOH (3.5 mL) was heated in a microwave oven at 60° C. for 50 min. The resultant solution was evaporated to dryness. Toluene was added to the residual solid and evaporated. The orange solid was used without further purification. LCMS (Method B): RT=3.85 min, [M+H]+=366.

Workup

customThe resultant solution was evaporated to dryness
additionToluene was added to the residual solid
customevaporated
customThe orange solid was used without further purification

Sources & evidence

ORD record: ord-4c0b62a6f66547669b62ab2b6c292b52
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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