Cesium carbonate → tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 871092ノート

反応式

HRID 871092 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]=2)O1.[Cl:29][C:30]1[C:31]2[CH:38]=[C:37](I)[N:36]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:32]=2[N:33]=[CH:34][N:35]=1>O1CCCC1.O.C(OCC)(=O)C>[Cl:29][C:30]1[C:31]2[CH:38]=[C:37]([C:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH:16]=3)[N:36]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:32]=2[N:33]=[CH:34][N:35]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

生成物 1

HCID 58709981tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

A mixture of cesium carbonate (7.45 g, 22.88 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.778 g, 0.95 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (3.98 g, 12.87 mmol), and 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (5 g, 9.53 mmol) in tetrahydrofuran (50 mL) and water (8.33 mL) was heated at 65° C. for 16 hours, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP), eluting with a gradient of 5-80% ethyl acetate in heptanes to provide the title compound. ESI MS: 497.1 (M+Na)+.

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP)
  6. washeluting with a gradient of 5-80% ethyl acetate in heptanes

出典と根拠

ORDレコード
ord-e5a01929a295416893fe28397bcf7091
出典データセット
uspto-grants-2015_03
特許番号
US08969375B2

反応ノート

読み込み中…