Phosphorus oxybromide → HCID 67312735, compound

HRID 1890346Notes

Reaction equation

HRID 1890346 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16](=O)[NH:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:28])=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16]([Br:28])=[N:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 67312866HCID 67312866, compound

Product 1

HCID 67312735HCID 67312735, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-(benzyloxy)-3-(2-fluorophenyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (244 mg, 0.728 mmol) and POBr3 (2.086 g, 7.28 mmol) in toluene (30 mL) was heated to 100° C. for 72 h in a 40 mL sealed scintillation vial. After cooling to room temperature, the reaction mixture was poured into saturated aqueous NaHCO3 (200 mL) and the mixture was extracted with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound (148 mg). LCMS m/z=398.0 [M+H]+.

Workup

  1. customsealed scintillation vial
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-91866c622e4b4b4abef25c6d0f4ff149
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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