Sodium Carbonate → 4-fluoro-3-(6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline

HRID 527998ノート

反応式

HRID 527998 の反応式
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH:16]=3)[N:8](S(C3C=CC=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.[F:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=1[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH:16]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 722211464-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)anilineHCID 904181484-chloro-6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 904184944-fluoro-3-(6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)aniline

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of Example 29A (1.10 g, 2.429 mmol), 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (749 mg, 3.16 mmol), and bis(triphenylphosphine)palladium(II) dichloride (170 mg, 0.243 mmol) in 7/2/3 1,2-dimethyoxyethane/ethanol/water (30 mL) was added sodium carbonate (3.64 mL, 7.29 mmol). The mixture was heated at 90° C. for 1 hour, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in 30 mL dioxane, treated with 6M sodium hydroxide (4.05 mL, 24.29 mmol), heated at 100° C. for 1 hour, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with ethyl acetate to give the title compound. MS (ESI+) m/z 388.2 (M+H)+.

後処理

  1. temperaturecooled
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 30 mL dioxane
  7. temperatureheated at 100° C. for 1 hour
  8. temperaturecooled
  9. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-bb6b76ef0c834ac38d52094837843ffb
出典データセット
uspto-grants-2016_05
特許番号
US09346813B2

反応ノート

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