Hydrochloric Acid → 9-(3-iodo-4-methylphenyl)-5,9-dihydro-3H-furo(3,4-b)pyrano(4,3-e)pyridine-1,8(4H,7H)-dione

HRID 987386Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13](C)[NH:12][C:11]3[CH2:20][O:21][CH2:22][C:23](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8].N1C=CC=CC=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:23](=[O:24])[CH2:22][O:21][CH2:20][C:11]=3[NH:12][C:13]3[CH2:18][O:17][C:15](=[O:16])[C:14]2=3)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: -10 °C

Procedure

The product from Example 5A (0.60 g, 1.4 mmol) in chloroform (10 mL) under a nitrogen atmosphere was treated with pyridine (0.13 mL, 1.6 mmol) and pyridinium tribromide (0.48 g, 1.5 mmol) at −10° C. After stirring at −10° C. for 2 hours, the mixture was allowed to warm to ambient temperature and then was treated with 1M HCl and extracted with chloroform. The chloroform layer was dried (MgSO4), filtered, concentrated, heated to 130° C. under nitrogen for 1 hour and cooled to ambient temperature. Purification of the residue by chromatography on silica gel eluting with 10% methanol in dichloromethane provided the title compound (0.28 g).

Workup

temperatureto warm to ambient temperature
extractionextracted with chloroform
dry with materialThe chloroform layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
temperatureheated to 130° C. under nitrogen for 1 hour
temperaturecooled to ambient temperature
customPurification of the residue by chromatography on silica gel eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-4d438c3a71a44275848944bd827df33f
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632418B2

Reaction notes

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