Potassium Carbonate → [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone

HRID 875439Notes

Reaction equation

HRID 875439 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([C:11]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[C:4]([Cl:20])[CH:3]=1.C(OC([N:28]1[C:32]([CH3:33])=[C:31](B(O)O)[C:30]([CH3:37])=[N:29]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[Cl:8][C:6]1[CH:7]=[C:2]([C:31]2[C:32]([CH3:33])=[N:28][NH:29][C:30]=2[CH3:37])[CH:3]=[C:4]([Cl:20])[C:5]=1[C:9]([C:11]1[C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 467398121-BOC-3,5-dimethylpyrazole-4-boronic acidHCID 71061835(4-Bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone

Product 1

HCID 86720645[2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanoneYield 23.1%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4-bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (50 mg, 0.135 mmol), [1-(tert-butoxycarbonyl)-3,5-dimethyl-1H-pyrazol-4-yl]boronic acid (52 mg, 0.162 mmol), potassium carbonate (55 mg, 0.4 mmol), water (0.5 mL) and 1,1′bis(diphenylphosphino)ferrocene]dichloropalladium (II) (11 mg, 0.0135 mmol) in 1,4 dioxane (2 mL) was heated at 100° C. for 2 hours in a sealed vial. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting crude mass was purified by preparative thin layer chromatography using methanol in dichloromethane (10%) to afford [2,6-dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)phenyl](1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (0.012 g, 23%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe resulting crude mass was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-3e257a33c46b4a7089fedaa33d414efe
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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