Sodium Carbonate → 1-(4-Methoxybenzyl)-4-phenylphthalazine

HRID 911121노트

반응식

HRID 911121 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](Cl)=[N:10][N:9]=2)=[CH:5][CH:4]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:10][N:9]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 866141621-Chloro-4-(4-methoxybenzyl)phthalazine

생성물 1

HCID 667316721-(4-Methoxybenzyl)-4-phenylphthalazine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To 1,1′-bis(diphenylphosphoino)ferrocene-palladium dichloride (0.046 g, 0.063 mmol), 1-(4-methoxybenzyl)-4-chlorophthalazine (0.360 g, 1.3 mmol), and phenylboronic acid (0.39 g, 3.2 mmol) was added dioxane (4.0 mL) and sodium carbonate (2.0M, aq) (1.9 ml, 3.8 mmol). The resulting mixture was heated to 100° C. in a sealed tube for 1 hour. The reaction was diluted with EtOAc and extracted with water and brine. The organic layers were dried over sodium sulfate, filtered, concentrated, and the crude was purified by ISCO silica gel chromatography (10-100% EtOAc/hexanes, 40 g column). Concentrated the product fractions to yield 1-(4-methoxybenzyl)-4-phenylphthalazine as a light yellow solid. MS m/z=327 [M+1]+. Calc'd for C22H18N2O: 326.40.

후처리

  1. extractionextracted with water and brine
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe crude was purified by ISCO silica gel chromatography (10-100% EtOAc/hexanes, 40 g column)
  6. concentrationConcentrated the product fractions

출처 및 근거

ORD 기록
ord-5098a6de61fe42df8ae41413f7422deb
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022221B2

반응 노트

불러오는 중…