Phosphorus oxybromide → HCID 86669025, compound

HRID 2366300Notes

Reaction equation

HRID 2366300 reaction equation
[Br:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[S:9][C:4]=2[CH:5]=[N+:6]([O-])[CH:7]=1.P(Br)(Br)([Br:22])=O.C([O-])(O)=O.[Na+]>ClCCCl>[Br:22][C:5]1[C:4]2[S:9][C:10]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[N:11][C:3]=2[C:2]([Br:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 66801400HCID 66801400, compound

Product 1

HCID 86669025HCID 86669025, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 7-bromo-2-(2-chloro-6-fluoro-phenyl)-5-oxido-thiazolo[5,4-c]pyridin-5-ium (2.0 mmol, 720 mg) in 1,2-dichloroethane (30 mL) was added POBr3 (8.0 mmol, 2.3 g). The mixture was heated at 70° C. for 3 hours. The mixture was cooled to room temperature, and sat. NaHCO3 solution was added. The aqueous layer was extracted with DCM. The combined organics were dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel chromatography (0-15% EtOAc/hexane) to give the title compound as a white solid (600 mg, 71% yield). 1H NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 7.49 (dd, J=14.2, 8.0 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.19 (t, J=8.7 Hz, 1H). LCMS (ESI) m/z 422.9 [M+H+].

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-35582ce436384283a3294a57b1e8bfeb
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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