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

HRID 593997

反応式

HRID 593997 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178477754HCID 178477754、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c9be55960b5423f80cca06831ca01a2
出典データセット
uspto-grants-2016_01
特許番号
US09242961B2

関連ノート

読み込み中…