Toluene → 1-[(2E)-3-(3,4-dichlorophenyl)prop-2-en-1-yl]-1H-indole-2,3-dione

HRID 252616

反応式

HRID 252616 の反応式
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[C:5]1=[O:14])[CH:2]=[CH2:3].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:17]=1[Cl:23].C1(C)C=CC=CC=1.C1(N(C)C2CCCCC2)CCCCC1>C(Cl)Cl.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:15][C:16]1[CH:21]=[C:20](/[CH:3]=[CH:2]/[CH2:1][N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:13])[C:5]2=[O:14])[CH:19]=[CH:18][C:17]=1[Cl:23]

参加物

7

反応物 4

HCID 1140TolueneHCID 24210N-Methyl dicyclohexylamineHCID 88591Benzene, 1,2-dichloro-4-iodo-HCID 17135631-Allylisatin

生成物 1

HCID 248207811-[(2E)-3-(3,4-dichlorophenyl)prop-2-en-1-yl]-1H-indole-2,3-dione収率 84%

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of 1-allyl-1H-indole-2,3-dione (1.00 g, 5.34 mmol), Pd(P(t-Bu)3)2 (0.0819 g, 0.16 mmol), 1,2-dichloro-4-iodobenzene (1.458 g, 5.34 mmol), dry toluene (10 mL), and N-cyclohexyl-N-methylcyclohexanamine (1.23 mL, 5.86 mmol) in an oven-dried sealed tube under an atmosphere of N2 was heated for 16 h at 80° C. The reaction was cooled, diluted with CH2Cl2, and loaded directly onto a silica gel column that had been packed with CH2Cl2. The column was eluted with a gradient of 100% CH2Cl2 to 95:5 CH2Cl2:EtOAc. The appropriate fractions were combined to provide the title compound as an orange solid (1.489 g, 84%). 1H NMR (600 MHz, CHLOROFORM-D) δ ppm 4.52 (d, J=5.9 Hz, 2H), 6.19 (dt, J=15.9, 5.9 Hz, 1H), 6.56 (d, J=15.6 Hz, 1H), 6.91 (d, J=7.9 Hz, 1H), 7.09-7.20 (m, 2H), 7.37 (d, J=8.2 Hz, 1H), 7.42 (s, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.64 (d, J=7.4 Hz, 1H).

後処理

  1. customsealed tube under an atmosphere of N2
  2. temperatureThe reaction was cooled
  3. washThe column was eluted with a gradient of 100% CH2Cl2 to 95:5 CH2Cl2

出典と根拠

ORDレコード
ord-7ae5152143c24049bebe2da54caadf37
出典データセット
uspto-grants-2011_01
特許番号
US07868181B2

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