Dichloromethane → HCID 58276410, 화합물

HRID 70334노트

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HRID 70334 반응식
[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]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 58276270HCID 58276270, 화합물

생성물 1

HCID 58276410HCID 58276410, 화합물

시약·촉매·용매 1

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

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온도
135 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3290803bae5044bf80a17e12a7d2ed01
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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