Styrene → (E)-3-methyl-7-styrylquinazolin-4(3H)-one

HRID 1619404Notes

Reaction equation

HRID 1619404 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[N:7]([CH3:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][N:7]1[C:6](=[O:13])[C:5]2[C:10](=[CH:11][C:2](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:3][CH:4]=2)[N:9]=[CH:8]1

Participants

9

Reactant 4

HCID 7501StyreneHCID 10796Cesium carbonateHCID 80271Tri-o-tolylphosphineHCID 585745147-Bromo-3-methyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 58574275(E)-3-methyl-7-styrylquinazolin-4(3H)-oneYield 33.6%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-bromo-3-methylquinazolin-4(3H)-one (100 mg, 0.42 mmol), styrene (109 mg, 1.05 mmol), Cs2CO3 (163.8 mg, 0.5 mmol), Bu4NBr (135 mg, 0.42 mmol), tri(o-tolyl)phosphine (128 mg, 0.42 mmol), and Pd(OAc)2 in DMF (5 mL) was stirred at 100° C. for 3 hours. After it was cooled to room temperature, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (37 mg). MS (ESI): 263 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.15-8.12 (d, J=8.70 Hz, 1H), 7.85-7.82 (m, 2H), 7.69-7.67 (d, J=7.26 Hz, 2H), 7.57-7.30 (m, 5H), 3.49 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-06d07ab12127429cb85d4555f6d63b54
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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