Tetrahydrofuran → HCID 71253589、化合物

HRID 1775053ノート

反応式

HRID 1775053 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([Sn](C)(C)C)=[N:14][N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:10]3=[CH:11][N:12]=2)[CH:2]=1.Br[C:29]1[N:34]=[C:33]([F:35])[C:32]([Cl:36])=[CH:31][CH:30]=1.O1CCCC1.[F-].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.[Pd](Cl)Cl.[Cu]I>[Cl:36][C:32]1[CH:31]=[CH:30][C:29]([C:15]2[C:9]3[C:10](=[CH:11][N:12]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)[N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:14]=2)=[N:34][C:33]=1[F:35]

参加物

9

反応物 5

HCID 8028TetrahydrofuranHCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 71253848HCID 71253848、化合物HCID 722139976-Bromo-3-chloro-2-fluoropyridine

生成物 1

HCID 71253589HCID 71253589、化合物

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

反応条件

温度
45 °C

実験手順

To a solution of 5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-3-(trimethylstannyl)-1H-pyrazolo[3,4-c]pyridine (1.3490 g, 2.7571 mmol) and 6-bromo-3-chloro-2-fluoropyridine (696.23 mg, 3.3086 mmol) in tetrahydrofuran (10 mL, 100 mmol) under Argon in a pressure tube was added Cesium fluoride (837.64 mg, 5.5143 mmol), Palladium(II) Chloride (24.446 mg, 0.13786 mmol), Copper(I) iodide (52.510 mg, 0.27571 mmol), and 1.000 M of Tri-tert-butylphosphine in Toluene (275.71 uL) at room temperature. The tube was sealed and the mixture was heated at 45° C. overnight. The mixture was cooled to room temperature, and filtered through Celite®. The filter cake was washed with ethyl acetate; the combined organic layer was washed with brine, dried with MgSO4, and then concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 3-(5-chloro-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine as a yellow oil, which solidified upon standing.

後処理

  1. customThe tube was sealed
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through Celite®
  4. washThe filter cake was washed with ethyl acetate
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica
  9. washeluted with 0 to 100% EtOAc in Heptane

出典と根拠

ORDレコード
ord-04640d17222d400dabd1ac7c93b3d8c9
出典データセット
uspto-grants-2016_02
特許番号
US09260425B2

反応ノート

読み込み中…