Boron tribromide → HCID 136346960, compound

HRID 1428932Notes

Reaction equation

HRID 1428932 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[C:11](=[O:20])[N:10]([CH2:21][C:22]([N:24]([CH3:35])[C:25]3[CH:34]=[CH:33][C:28]4[N:29]=[C:30]([CH3:32])[O:31][C:27]=4[CH:26]=3)=[O:23])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:20])[N:10]([CH2:21][C:22]([N:24]([CH3:35])[C:25]3[CH:34]=[CH:33][C:28]4[N:29]=[C:30]([CH3:32])[O:31][C:27]=4[CH:26]=3)=[O:23])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86298931HCID 86298931, compound

Product 1

HCID 136346960HCID 136346960, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(3-fluorophenyl)-7-methoxy-1-oxophthalazin-2(1H)-yl)-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (example 70) (4.0 g, 8.469 mmol) in DCM (30 mL) was added BBr3 (4.8 mL, 50.8 mmol) at 0° C. The reaction mixture was stirred at rt overnight then diluted with water (150 mL), neutralized with NaHCO3, then extracted with DCM (3×100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4, and concentrated to yield 2-(4-(3-fluorophenyl)-7-hydroxy-1-oxophthalazin-2(1H)-yl)-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (2.9 g, 74%) (459.36 [M+H]).

Workup

  1. extractionextracted with DCM (3×100 mL)
  2. washThe organic layer was washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f77a8a8409864887924fcf64e23f180b
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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