Cesium carbonate → 4'-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-3'-fluoro-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

HRID 571061ノート

反応式

HRID 571061 の反応式
[F:1][C:2]1[C:3]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[C:11]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[CH:10]2)=[N:4][CH:5]=[CH:6][C:7]=1I.[Cl:26][C:27]1[C:28](B2OC(C)(C)C(C)(C)O2)=[C:29]2[CH:35]=[CH:34][N:33]([Si](C(C)C)(C(C)C)C(C)C)[C:30]2=[N:31][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Cl:26][C:27]1[C:28]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([N:9]3[CH:14]=[CH:13][C:12](=[O:15])[C:11]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[CH:10]3)[C:2]=2[F:1])=[C:29]2[CH:35]=[CH:34][NH:33][C:30]2=[N:31][CH:32]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 453617775-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 674184733'-fluoro-4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

生成物 1

HCID 866802754'-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-3'-fluoro-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
135 °C

実験手順

To a room temperature solution of 132 mg (0.292 mmol) 3′-fluoro-4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one in 2 mL THF in a 5 mL microwave vial (Biotage) were added 253 mg (0.584 mmol) 5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, 1 mL 1.0 M cesium carbonate (1.0 mmol), and 23.8 mg (0.029 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The vial was sealed and the reaction mixture was heated at 135° C. under microwave irradiation for 15 minutes, then cooled. The organic layer was separated, washed with 1 mL water, dried over Na2SO4, filtered, stirred over Quadrapure TU resin (Aldrich), concentrated in vacuo, and used without further purification.

後処理

  1. customThe vial was sealed
  2. temperaturecooled
  3. customThe organic layer was separated
  4. washwashed with 1 mL water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customused without further purification

出典と根拠

ORDレコード
ord-d01eb79885d549308c062da0ba9abb8f
出典データセット
uspto-grants-2015_05
特許番号
US09024032B2

反応ノート

読み込み中…