Phosphorus oxybromide → HCID 68896885, compound

HRID 1783696Notes

Reaction equation

HRID 1783696 reaction equation
[CH3:1][C:2]([S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[NH:23][C:22](=O)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:25])=[CH:10][CH:9]=1)(=[O:7])=[O:6])([CH3:4])[CH3:3].P(Br)(Br)([Br:28])=O>O>[Br:28][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:25])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])(=[O:7])=[O:6])=[CH:9][CH:10]=2)[N:23]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 68895530HCID 68895530, compound

Product 1

HCID 68896885HCID 68896885, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[4-(2-methyl-propane-2-sulfonyl)-phenyl]-2,3-dihydro-phthalazine-1,4-dione (0.20 g, 0.56 mmol) and phosphorus oxybromide (0.48 g, 1.7 mmol) were stirred at 150° C. for 1 h. H2O (50 ml) was added after cooling to RT. Extraction with DCM, drying of the combined organic phases over Na2SO4, evaporation of the solvent and purification of the raw product by preparative HPLC yielded the desired compound (0.06 g, 18%). 1H-NMR: (400 MHz, D6-DMSO) 8.41 (1H, d), 8.07 (1H, d), 8.03-8.10 (4H, m), 7.80 (2H, d), 1.30 (9H, s); MS (API+)=423.0 (M+H)+.

Workup

  1. extractionExtraction with DCM
  2. dry with materialdrying of the combined organic phases over Na2SO4, evaporation of the solvent and purification of the raw product by preparative HPLC

Sources & evidence

ORD record
ord-56bb6c0eb99b40758d12cfcc7d6b1c8b
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

Loading…