Dichloromethane → HCID 58276410、化合物

HRID 70334ノート

反応式

HRID 70334 の反応式
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[N:8]1)=[O:4].[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:21]=[O:22])[CH:28]=3)=[CH:14][CH:13]=2)=[N:8]1)=[O:4]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 58276270HCID 58276270、化合物

生成物 1

HCID 58276410HCID 58276410、化合物

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
135 °C

実験手順

To a solution of [3-(4-bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethyl-propanoate (0.108 g, 0.32 mmol; IV-30), 3-formylphenyl boronic acid (0.099 g, 0.66 mmol), and PdCl2(dppf).CH2Cl2 (0.024 g, 0.029 mmol) was added 2M Na2CO3 (aq) (0.38 mL, 0.76 mmol). The mixture was subjected to microwave heating (135° C./50 min), cooled, and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (s, 9 H), 6.10 (s, 2 H), 7.63 (t, J=7.69 Hz, 1 H), 7.73 (d, J=8.06 Hz, 2 H), 7.90 (dd, J=14.65, 7.57 Hz, 2 H), 8.15 (m, 1 H), 8.23 (d, J=8.30 Hz, 2 H), 8.39 (s, 1 H), 10.10 (s, 1 H).

後処理

  1. temperaturecooled
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialwere dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-3290803bae5044bf80a17e12a7d2ed01
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

反応ノート

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