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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
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HRID 633559 반응식
[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
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참가 물질

5

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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

생성물 1

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

시약·촉매·용매 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매

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온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9cb8e2f89b8643aab3a689dcabd1e0b0
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321764B2

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