Cesium carbonate → 4-chloro-6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527997ノート

反応式

HRID 527997 の反応式
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1.O1CCCC1.O.[CH3:27][S:28]([N:31]1[CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33][CH2:32]1)(=[O:30])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:34]3[CH2:35][CH2:36][N:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH2:32][CH:33]=3)[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 21881883Oxolane--water (1/1)HCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidineHCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

生成物 1

HCID 904181484-chloro-6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (1.9 g, 4.53 mmol) in 6:1 tetrahydrofuran/water (60 mL) was added 1-(methylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (1.56 g, 5.43 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.37 g, 0.453 mmol) and cesium carbonate (3.54 g, 10.87 mmol). The mixture was heated at 50° C. overnight, 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. Purification by flash chromatography on silica (Analogix 280) eluting with a gradient of 10% to 60% ethyl acetate/hexanes gave the title compound. MS (ESI+) m/z 452.5 (M)+.

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. customPurification by flash chromatography on silica (Analogix 280)
  7. washeluting with a gradient of 10% to 60% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-2dad17fa01554ee489278255ef58a71f
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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