Phosphorus tribromide → HCID 86684804, compound

HRID 1527976Notes

Reaction equation

HRID 1527976 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:9][C:10]([C:12]2(OC)[CH:17]=[CH:16][CH:15]=[N+:14]([O-])[NH:13]2)=[O:11])=[CH:4][CH:3]=1.P(Br)(Br)Br.C(=O)([O-])[OH:33].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](=[O:33])[NH:14][N:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 86684805HCID 86684805, compound

Product 1

HCID 86684804HCID 86684804, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-6-(3-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-3-methoxypyridazine 1-oxide (679 mg, 1.59 mmol) and phosphorous tribromide (2.58 g, 9.53 mmol) in ethyl acetate (15 mL) was heated at reflux for 30 min, then after cooling poured onto ice water, neutralized with sat. aq. sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. After chromatography (SiO2; heptane-ethyl acetate gradient) the title compound was obtained (318 mg, 50%). White semisolid, MS: 397.1 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. temperatureafter cooling
  4. additionpoured onto ice water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6f3540c3a1944d0880b766e3d260a47a
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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