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

HRID 1619404노트

반응식

HRID 1619404 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-06d07ab12127429cb85d4555f6d63b54
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772301B2

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