Potassium Carbonate → 7-(4-chloro-1H-pyrazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridine

HRID 1157784Notes

Reaction equation

HRID 1157784 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[Cl:13][C:14]1[CH:15]=[N:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[CH:15]=[N:16][N:17]([C:2]2[N:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]3[CH:10]=[CH:9][NH:8][C:7]=23)[CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 275241H-Pyrazole, 4-chloro-HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 207912447-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 595114457-(4-chloro-1H-pyrazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridineYield 72.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a sealable flask containing 7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine (1 g, 4.40 mmol) was added 4-chloro-1H-pyrazole (0.903 g, 8.81 mmol), potassium carbonate (2.435 g, 17.62 mmol), copper(I) iodide (0.419 g, 2.202 mmol), and trans-1,2-bis(methylamino)cyclohexane (0.626 g, 4.40 mmol). The mixture was diluted with 1,4-Dioxane (15 mL) and was sealed and heated to 100° C. for 3 h. The mixture was cooled to rt and was filtered through a pad of celite to remove any solids. The organic solution as concentrated under reduced pressure, and the residue was purified by flash chromatography to give 7-(4-chloro-1H-pyrazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridine (0.79 g, 3.18 mmol, 72.1% yield) as an off-white solid. LCMS: m/e 249.12 (M+H)+, ret time 2.851 min (method 4).

Workup

  1. customwas sealed
  2. temperatureThe mixture was cooled to rt
  3. filtrationwas filtered through a pad of celite
  4. customto remove any solids
  5. concentrationThe organic solution as concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b6c0e354a9624b31bf1b51c6017af5e3
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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