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

HRID 1619404ノート

反応式

HRID 1619404 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-06d07ab12127429cb85d4555f6d63b54
出典データセット
uspto-grants-2014_07
特許番号
US08772301B2

反応ノート

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