Benzyl Bromide → HCID 59002963, compound

HRID 561132Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[C:5]([N+:23]([O-:25])=[O:24])=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[C:13]=1[F:14])[NH:10][CH:9]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]2=[O:22].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:10]1[C:11]2[C:6](=[C:5]([N+:23]([O-:25])=[O:24])[C:4]([F:3])=[C:13]([F:14])[C:12]=2[O:15][CH3:16])[C:7](=[O:22])[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaH (1.17 g, 29.3 mmol, 60% in oil) in DMF (50 mL) was cooled to 0° C. and treated dropwise with ethyl 6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (8.0 g, 24.4 mmol) in DMF (50 mL). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 30 min. To the solution was added benzyl bromide (4.4 mL, 36.9 mmol) and stirred over night. The reaction mixture was poured into ice-water and extract with CH2Cl2. The organic layer washed with water, brine, and then dried. The solvent was removed and the crude product was purified by column chromatography (Hexane:EtOAc 3:1 →1:1) to yield ethyl 1-benzyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.74 g, 27%) as a pale yellow solid.

Workup

stirringstirred over night
extractionextract with CH2Cl2
washThe organic layer washed with water, brine
customdried
customThe solvent was removed
customthe crude product was purified by column chromatography (Hexane:EtOAc 3:1 →1:1)

Sources & evidence

ORD record: ord-f40d466ef3c74435b2c028f1f898f52b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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