Reaction equation
B.[Na].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:31]=[CH:30][C:19]4[O:20][CH2:21][C:22]5[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=5[C:24](=[O:25])[C:18]=4[CH:17]=3)=[N:11]2)=[CH:6][C:5]=1[F:32]>CO>[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][O:15][C:16]3[CH:31]=[CH:30][C:19]4[O:20][CH2:21][C:22]5[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=5[CH:24]([OH:25])[C:18]=4[CH:17]=3)=[N:11]2)=[CH:6][C:5]=1[F:32]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.5 g of sodium boron hydride was added to 2.58 g of 2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-11-oxo-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 34 suspended in 70 ml of methanol and the mixture was stirred at room temperature for 11 hours. During stirring, 0.35 g of sodium boron hydride was added to the mixture twice. After completion of the reaction, the solvent was removed under reduced pressure, ice water was added to the residue and the mixture was extracted with methylene chloride. Then, the organic layer was washed with water and then dried over anhydrous sodium sulfate and the solvent was removed. The resulting solid was washed with a methylene chloride-hexane mixed solution to obtain 1.87 g of the title compound. Mass (CI); m/z=422 (M+ +1)
Workup
- customobtained in Reference example 34
- stirringDuring stirring
- customAfter completion of the reaction
- customthe solvent was removed under reduced pressure, ice water
- additionwas added to the residue
- extractionthe mixture was extracted with methylene chloride
- washThen, the organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed
- washThe resulting solid was washed with a methylene chloride-hexane mixed solution
Sources & evidence
- ORD record
- ord-de0b38d424da4514b19f65882da930be
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591752
Linked notes
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