Water → HCID 71061536, compound

HRID 875469Notes

Reaction equation

HRID 875469 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([N:11]2[C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH:13]=[CH:12]2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.O>C(#N)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[Cl:8][C:6]1[CH:7]=[C:2]([C:29]2[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=2)[CH:3]=[C:4]([Cl:20])[C:5]=1[C:9]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:13]=[CH:12]1)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 71061918HCID 71061918, compound

Product 1

HCID 71061536HCID 71061536, compound

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[3,2-c]pyridin-1-yl)methanone (0.05 g, 0.135 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.011 g, 0.0135 mmol), potassium carbonate (0.055 g, 0.40 mmol), pyridine-3-boronic acid (1.1 equiv) and water (0.5 mL) in acetonitrile (2.5 mL) was heated in a sealed vial under microwave irradiation at 110° C. for 25 minutes. Acetonitrile was removed under vacuum and the residue was diluted with water (25 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with water, dried over anhydrous sodium sulphate and concentrated to give crude product which was purified by silica gel column chromatography using ethyl acetate and hexane as eluent to yield [2,6-dichloro-4-(pyridin-3-yl)phenyl](1H-pyrrolo[3,2-c]pyridin-1-yl)methanone.

Workup

  1. temperaturewas heated in a
  2. customsealed vial under microwave irradiation at 110° C. for 25 minutes
  3. customAcetonitrile was removed under vacuum
  4. additionthe residue was diluted with water (25 mL)
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. washThe combined organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. customto give crude product which
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e80d0e83a48d464392a944589a423bb8
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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