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 571061노트

반응식

HRID 571061 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
135 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d01eb79885d549308c062da0ba9abb8f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024032B2

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