Sodium Carbonate → 4-Phenyl-N-(2-(2-(pyridin-4-yl)phenoxy)pyrimidin-5-yl)phthalazin-1-amine

HRID 911182

반응식

HRID 911182 반응식
Br[C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:14][N:13]=2)=[CH:7][N:6]=1.[N:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>CCOC(C)=O.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:22]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([NH:11][C:8]3[CH:7]=[N:6][C:5]([O:4][C:3]4[CH:28]=[CH:29][CH:30]=[CH:31][C:2]=4[C:35]4[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=4)=[N:10][CH:9]=3)=[N:13][N:14]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734379(Pyridin-4-yl)boronic acidHCID 57756263N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine

생성물 1

HCID 577562364-Phenyl-N-(2-(2-(pyridin-4-yl)phenoxy)pyrimidin-5-yl)phthalazin-1-amine

시약·촉매·용매 3

HCID 178477754HCID 178477754, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

In an argon-purged sealed tube, N-(2-(2-bromophenoxy)pyrimidin-5-yl)-4-phenylphthalazin-1-amine (150 mg, 319 μmol), pyridin-4-ylboronic acid (157 mg, 1.27 μmol), Pd(DPPF)Cl2 (47 mg, 64 μmol), sodium carbonate (239 μl, 478 μmol), and 1,4-dioxane (1.60 ml, 319 μmol) were added. The reaction was stirred at RT for 5 min. The tube was sealed and heated to 100° C. for 18 h. After 16 h, the reaction was cooled to RT, diluted with EtOAc and 10 mL of water. The product was extracted into EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography on silica gel using 60:40 DCM:(90:10:1 DCM:MeOH:NH4OH). The resulting light brown solid was dissolved in 15 mL of DCM, the solvent were removed under vacuum, affording the title compound as a light brown solid. MS Calcd for C29H20N6O: [M]+=468. Found: [M+H]+=469.

후처리

  1. customIn an argon-purged
  2. customsealed tube
  3. customThe tube was sealed
  4. temperatureheated to 100° C. for 18 h
  5. waitAfter 16 h
  6. temperaturethe reaction was cooled to RT
  7. extractionThe product was extracted into EtOAc
  8. washThe organic layer was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was purified by column chromatography on silica gel using 60:40 DCM
  13. dissolutionThe resulting light brown solid was dissolved in 15 mL of DCM
  14. customthe solvent were removed under vacuum

출처 및 근거

ORD 기록
ord-7e76ce9502554866a04be52d9dd48cb8
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022221B2

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