Boron tribromide → HCID 22106060, compound

HRID 1456373Notes

Reaction equation

HRID 1456373 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)=[C:4]([NH:20][C:21]([NH:23][C:24]2[C:29]([CH:30]([CH3:32])[CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[CH:33]([CH3:35])[CH3:34])=[O:22])[C:3]1=[O:36].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[C:4]([NH:20][C:21]([NH:23][C:24]2[C:29]([CH:30]([CH3:31])[CH3:32])=[CH:28][CH:27]=[CH:26][C:25]=2[CH:33]([CH3:35])[CH3:34])=[O:22])[C:3]1=[O:36]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9848186HCID 9848186, compound

Product 1

HCID 22106060HCID 22106060, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-methyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (1310 mg, 2.7 mmol) in methylene chloride (20 ml) was added dropwise boron tribromide (1.7 g, 6.75 mmol) at 0° C., and the mixture was stirred for 6 hours. The mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with methylene chloride. The extract was washed with water, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, purified by silica gel column chromatography (3% methanol in chloroform), and crystallized from diethyl ether/hexane to give the title compound (830 mg, 1.76 mmol) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe residue was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography (3% methanol in chloroform)
  7. customcrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-4ac5d1aa257c49f38d3fc0347391125d
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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