Phosphorus oxybromide → HCID 58149871, compound

HRID 2192496Notes

Reaction equation

HRID 2192496 reaction equation
P(Br)(Br)([Br:3])=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:23]=3[CH:24]=[CH:25][NH:26][C:27]4=O)[N:18]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15].C([O-])(O)=O.[Na+]>ClCCCl>[Br:3][C:27]1[C:28]2[C:23](=[C:22]([C:19]3[N:18]=[C:17]([C:9]4[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:16])[CH3:15])=[C:7]([Cl:6])[CH:8]=4)[O:21][N:20]=3)[CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 581499065-[5-[3-Chloro-4-(1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl]-1(2H)-isoquinolinone

Product 1

HCID 58149871HCID 58149871, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phosphorus oxybromide (3.9 g) was added to a suspension of 5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1(2H)-isoquinolinone (D39; 2.6 g) in 1,2-dichloroethane (300 ml) at room temperature. The resulting suspension was heated under reflux and stirred overnight. The reaction mixture was poured into cold sat. aq. NaHCO3 and the organic layer was separated. The aqueous layer was extracted with DCM (100 ml). The organic fractions were combined and dried over anhydrous sodium sulphate. The dried solution was filtered and the filtrate was concentrated to give the title compound (1 g).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with DCM (100 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationThe dried solution was filtered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8d8b8ac2026f460d8c6b5d46a7434653
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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