Phosphorus tribromide → HCID 22064012, compound

HRID 1827743Notes

Reaction equation

HRID 1827743 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:14]2[N:15]=[C:16]([CH3:20])[CH:17]=[C:18](O)[C:13]2=[CH:12][C:11]=1[CH3:21].P(Br)(Br)[Br:23].C([O-])(O)=O.[Na+]>BrC1C=CC=CC=1.C(Cl)(Cl)Cl>[Br:23][C:18]1[C:13]2[N:14]([C:10]([C:3]3[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=3[Cl:1])=[C:11]([CH3:21])[CH:12]=2)[N:15]=[C:16]([CH3:20])[CH:17]=1

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 178488531HCID 178488531, compound

Product 1

HCID 22064012HCID 22064012, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7961BromobenzeneSolvent

Procedure

A solution of 7-(2-chloro-4-methoxyphenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazin-4-ol (2.89 g, 9.50 mmol) and phosphorus tribromide (4.20 mL, 12.0 g, 44.0 mmol) in bromobenzene (50.0 mL) was refluxed for 1 h. After cooling down to room temperature, the mixture was diluted with CHCl3. Saturated NaHCO3 solution was added to neutralize and separated immediately. The aqueous layer was extracted with CHCl3 (2×). The combined CHCl3 solution was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (silica gel, 1/5 EtOAc/heptane) to afford 3.13 g (90%) of yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.34 (d, J=8.6 Hz, 1H), 7.13 (d, J=2.6 Hz, 1H), 6.98 (dd, J=8.6, 2.6 Hz, 1H), 6.73 (s, 1H), 6.60 (s, 1H), 3.91 (s, 3H), 2.40 (s, 3H), 2.27 (s, 3H); MS m/z 366.99 (M++H).

Workup

  1. customseparated immediately
  2. extractionThe aqueous layer was extracted with CHCl3 (2×)
  3. dry with materialThe combined CHCl3 solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-39eee4b6167e447690fb39cbd39a268a
Source dataset
uspto-grants-2006_06
Patent number
US07056920B2

Reaction notes

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