Boron tribromide → HCID 136132570, compound

HRID 1626025Notes

Reaction equation

HRID 1626025 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[O:8][C:9]1[N:10]=[C:11]([O:28][CH2:29][CH2:30][CH3:31])[C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([O:25]C)=[C:20]([CH3:27])[CH:19]=3)[O:15][C:13]=2[N:14]=1.C(=O)([O-])O.[Na+]>ClCCl>[F:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[O:8][C:9]1[N:10]=[C:11]([O:28][CH2:29][CH2:30][CH3:31])[C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[C:20]([CH3:27])[C:21]([OH:25])=[C:22]([CH3:24])[CH:23]=3)[O:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 53311549HCID 53311549, compound

Product 1

HCID 136132570HCID 136132570, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 ml of a 1 M solution of boron tribromide in dichloromethane was slowly added to an ice-cooled solution of 145 mg of 5-(2-fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-7-propoxy-oxazolo[5,4-d]pyrimidine in 8 ml of dichloromethane. The mixture was stirred for 2 h while maintaining ice cooling, and another 1 h at room temperature. Then a saturated solution of sodium hydrogencarbonate was carefully added. Extraction with dichloromethane, drying over sodium sulfate, filtration and removal of the solvent in vacuo gave 126 mg of the title compound.

Workup

  1. temperaturewhile maintaining ice cooling
  2. customanother 1 h
  3. customat room temperature
  4. extractionExtraction with dichloromethane
  5. dry with materialdrying over sodium sulfate, filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-ca269bf1d19d4209b1a79387598f3739
Source dataset
uspto-grants-2014_07
Patent number
US08785439B2

Reaction notes

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