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1,4-Dioxane → 5-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

HRID 1642521
ノート
印刷プレビュー

反応式

HRID 1642521 の反応式
I[C:2]1[C:7]2[C:8]3[C:9]([NH:15][C:6]=2[C:5](=[O:16])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:3]=1)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=3.[CH2:26]([S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])[CH3:27].O1CCOCC1>C(Cl)Cl>[CH2:26]([S:28]([C:31]1[CH:36]=[C:35]([C:2]2[C:7]3[C:8]4[C:9]([NH:15][C:6]=3[C:5](=[O:16])[N:4]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:3]=2)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=4)[CH:34]=[CH:33][CH:32]=1)(=[O:29])=[O:30])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 164271023-Ethylsulfonylphenylboronic acidHCID 588800935-Iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8h-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

生成物 1

HCID 588800415-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
150 °C

実験手順

In an appropriate microwave reaction vessel was placed, 5-iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido[4′,3′:4,5]pyrrolo [2,3-b]pyridin-8-one (8.0 g, 17.967 mmol), 3-(ethylsulfonyl)phenyl boronic acid (4.62 g, 21.562 mmol), and Tetrakis(triphenylphosphine)Pd(0) (6.23 g, 5.390 mmol). The solids were then suspended in a dioxane/saturated K2CO3 solution (40.0 mL, 4/1) and the mixture was heated in a large scale CEM microwave for 20 minutes at 150° C. The reaction mixture was diluted with DCM (400 mL), then filtered off undissolved solids. The organic layer was washed with brine (300 mL), dried with MgSO4, filtered and concentrated in vacuo affording an orange solid. The crude solid was washed with a hot ethyl acetate/hexanes solution (400 ml, 1/1) followed by a hot ethanol/DCM solution (400 mL, 4/1). The product was isolated by filtration, washed with ether and dried under vacuum affording an off-white solid. (6.83 g, 78%) 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (t, J=7.45 Hz, 3 H) 2.44 (s, 3 H) 3.20 (q, J=7.33 Hz, 2 H) 3.80 (s, 3 H) 5.37 (s, 2 H) 6.90 (d, J=8.59 Hz, 2 H) 7.16 (s, 1 H) 7.37 (d, J=8.59 Hz, 3 H) 7.75 (t, J=7.71 Hz, 1 H) 7.78-7.87 (m, 2 H) 8.03 (d, J=7.58 Hz, 1 H) 8.12 (s, 1 H) 8.43 (s, 1 H). ESI-MS: m/z 488.3 (M+H)+.

後処理

  1. customIn an appropriate microwave reaction vessel
  2. filtrationfiltered off undissolved solids
  3. washThe organic layer was washed with brine (300 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customaffording an orange solid
  8. washThe crude solid was washed with a hot ethyl acetate/hexanes solution (400 ml, 1/1)
  9. customThe product was isolated by filtration
  10. washwashed with ether
  11. customdried under vacuum
  12. customaffording an off-white solid

出典と根拠

ORDレコード
ord-61d663d09823476c8ed7023b055bb8c1
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08119655B2

反応ノート

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