Selectfluor → HCID 58574868, compound

HRID 1619319Notes

Reaction equation

HRID 1619319 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[N:7]3[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[N:7]3[CH2:15][C:14]([CH3:16])([CH3:17])[CH2:13][CH:12]([F:20])[C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 58574356HCID 58574356, compound

Product 1

HCID 58574868HCID 58574868, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-bromo-8,8-dimethyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (0.1 g, 0.327 mmol, 1 equiv) in DMF (5 mL), Selectfluor (0.12 g, 0.327 mmol, 1 eq) was added. The reaction mixture was heated to 90° C. and stirred for 3 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3×50 mL), dried over Na2SO4. After filtration and concentration, 80 mg of the desired product was obtained, which was directly used for the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-28738799130f4c54aa3dd55fa310f7e7
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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