Boron tribromide → HCID 25165679, compound

HRID 2167477Notes

Reaction equation

HRID 2167477 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)=[CH:6][NH:7]2.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)=[CH:6][NH:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 251656785-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Product 1

HCID 25165679HCID 25165679, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (5 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (249 mg, 0.76 mmol) was cooled to −10° C. in a methanol-ice bath. A 1N boron tribromide (4.08 ml) was added thereto, and the mixture was stirred at room temperature for 6 hours. Ice water and dichloromethane were added to the reaction mixture, and the resultant insoluble matter was collected by filtration. The filtrate was separated and the organic layer was concentrated under reduced pressure. The residue and the substance remaining on the filter were mixed, and the mixture was purified by silica gel column chromatography (dichloromethane:methanol=60:1→25:1). The purified product was concentrated under reduced pressure. Ethyl acetate was added to crystallize the residue. The crystals were collected by filtration, washed with ethyl acetate, and then dried to thereby obtain 220 mg of powdery pale yellow 5-fluoro-3-(4-hydroxyphenyl)-8-propoxy-1H-quinolin-4-one (yield: 92%).

Workup

  1. filtrationthe resultant insoluble matter was collected by filtration
  2. customThe filtrate was separated
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. additionwere mixed
  5. customthe mixture was purified by silica gel column chromatography (dichloromethane:methanol=60:1→25:1)
  6. concentrationThe purified product was concentrated under reduced pressure
  7. additionEthyl acetate was added
  8. customto crystallize the residue
  9. filtrationThe crystals were collected by filtration
  10. washwashed with ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-c23bc5c2207d4a85b829a9fe7ed1d32b
Source dataset
uspto-grants-2015_06
Patent number
US09045464B2

Reaction notes

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