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Potassium Phosphate, Tribasic → 3-(2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridin-3-yl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 633559
ノート
印刷プレビュー

反応式

HRID 633559 の反応式
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][N:9]([CH3:21])[C:8]=12.Br[C:23]1[C:24]([O:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[F:42])=[N:25][CH:26]=[C:27]([CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:42][C:36]1[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=1[O:34][C:24]1[C:23]([C:11]2[C:7]3[C:8](=[C:3]([O:2][CH3:1])[N:4]=[CH:5][CH:6]=3)[N:9]([CH3:21])[CH:10]=2)=[CH:28][C:27]([CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 867210783-Bromo-2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridineHCID 903879807-methoxy-1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 904160973-(2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridin-3-yl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine収率 102.7%

試薬・触媒・溶媒 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒

反応条件

温度
60 °C

実験手順

The product from Example 59A (0.061 g, 0.212 mmol), the product from Example 60E (0.08 g, 0.212 mmol), tris(dibenzylideneacetone)dipalladium(0) (5.8 mg, 6.35 μmol), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (6.2 mg, 0.021 mmol) and potassium phosphate (0.157 g, 0.74 mmol) were combined and sparged with argon for 15 minutes. Meanwhile a solution of 4:1 dioxane/water (2 mL) was sparged with nitrogen for 15 minutes and transferred by syringe into the reaction vessel under argon. The mixture was stirred at 60° C. for 2 hours and partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), treated with 3-mercaptopropyl functionalized silica gel, filtered, and concentrated to afford the title compound (0.1 g, 100%).

後処理

  1. customsparged with argon for 15 minutes
  2. customMeanwhile a solution of 4:1 dioxane/water (2 mL) was sparged with nitrogen for 15 minutes
  3. customtransferred by syringe into the reaction vessel under argon
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (anhydrous Na2SO4)
  7. additiontreated with 3-mercaptopropyl functionalized silica gel
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-9cb8e2f89b8643aab3a689dcabd1e0b0
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321764B2

反応ノート

読み込み中…

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