1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22636375, compound

HRID 2061850Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([I:21])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][OH:14])[CH:9]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]2=[O:20].N12CCCN=C1CCCCC2>CN(C=O)C>[I:21][C:4]1[CH:5]=[C:6]2[C:11]3=[C:2]([O:14][CH2:13][CH2:12][N:10]3[CH:9]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]2=[O:20])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of ethyl 8-fluoro-1-(2-hydroxyethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 12, 20 mmol) in DMF (30 mL) was treated with 1.8-diazabicyclo[5.4.0]undec-7-ene (5.6 ml, 40 mmol) and the reaction mixture was stirred at 100° C. for 24 h. The solvent was then removed in vacuo and the residue was chromatographed on silica gel using 0-5% (0.2N ammonia in methanol) in dichloromethane to give 1.4 g (18%) of ethyl 9-iodo-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate as a white solid.

Workup

customThe solvent was then removed in vacuo
customthe residue was chromatographed on silica gel using 0-5% (0.2N ammonia in methanol) in dichloromethane

Sources & evidence

ORD record: ord-6f9ec15fd6684f45bc920f8e2a9c240f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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