Boron trifluoride → HCID 136343911, compound

HRID 2422629Notes

Reaction equation

HRID 2422629 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:31])[N:7]([CH3:30])[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:14][C:13]=3[O:28]C)=[N:9]2)=[CH:4][CH:3]=1.B(F)(F)F.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:31])[N:7]([CH3:30])[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:14][C:13]=3[OH:28])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 67243736HCID 67243736, compound

Product 1

HCID 136343911HCID 136343911, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Bromo-2-[2-methoxy-4-(3-piperidin-1-ylpropoxy)phenyl]-3-methylquinazolin-4(3H)-one (38.5 mg, 0.0792 mmol) was dissolved in CH2Cl2 (0.5 mL), stirred with cooling with ice, and boron trifluoride (1.0 M in CH2Cl2, 160 μL) was added thereto. After stirred for 20 hours at room temperature, the reaction solution was diluted with ethyl acetate, and with cooling with ice, it was poured into aqueous 1 N sodium hydroxide solution, and extracted with ethyl acetate. This was washed with saturated saline water and dried with magnesium sulfate. The organic layer was concentrated under reduced pressure, and purified through silica gel thin-layer chromatography (chloroform/methanol=9/1) to obtain the intended compound (9.5 mg, 25%) as a pale yellow solid.

Workup

  1. additionwas added
  2. stirringAfter stirred for 20 hours at room temperature
  3. temperaturewith cooling with ice, it
  4. extractionextracted with ethyl acetate
  5. washThis was washed with saturated saline water
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. custompurified through silica gel thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-d6f67c47614349e584fd556da8ce1e61
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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