Potassium Carbonate → HCID 22028196, compound

HRID 731564Notes

Reaction equation

HRID 731564 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[NH4+].[OH-].[Cu](I)I>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 53770783-Iodo-7-azaindole

Product 1

HCID 22028196HCID 22028196, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 3-iodo-1H-pyrrolo[2,3-b]pyridine (4.0 g, 16.4 mmol) in DMF is treated with 4-fluorobenzenethiol (2.09 mL, 19.7 mmol), potassium carbonate (3.40 g, 24.6 mmol), and copper iodide (4.21 g, 22.1 mmol). The reaction mixture is heated at 65° C. for 4 h, cooled, diluted with conc. aqueous NH4OH and extracted with ethyl acetate. The extracts are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Chromatography (1:50 methanol:CH2Cl2) of the residue, followed by methanol/H2O crystallization affords the title compound as an off-white solid, 3.56 g, mp 183-184° C., characterized by mass spectral and NMR analyses.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customChromatography (1:50 methanol:CH2Cl2) of the residue, followed by methanol/H2O crystallization

Sources & evidence

ORD record
ord-aa78c3cd910d44e698a0b863e5039278
Source dataset
uspto-grants-2009_09
Patent number
US07585873B2

Reaction notes

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