Potassium Carbonate → HCID 86706324, compound

HRID 2205936Notes

Reaction equation

HRID 2205936 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:10][C:4]=2[CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C.[Cu]I>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:10]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium Carbonate2×HCID 5642162-Bromo-5-methylpyridine2×HCID 867062766-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86706324HCID 86706324, compoundYield 46.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
210 °C

Procedure

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 84 mg 0.303 mmole) and 2-bromo-5-methylpyridine (78 mg, 0.45 mmole) were dissolved in DMA (2.1 ml) and potassium carbonate (60 mg, 0.42 mmole) and copper(I) iodide (12 mg, 0.066 mmole) were added. The reaction was placed under argon and heated by microwave at 210° C. for 60 minutes. Further 2-bromo-5-methylpyridine (49 mg) and potassium carbonate (40 mg) were added and the reaction again heated at 210° C. under microwave irradiation for 60 minutes. The reaction was taken up in ethyl acetate (30 mL) and the solution washed with water (3×10 mL) and brine. The aqueous was filtered through Celite and backwashed with ethyl acetate (10 mL). The combined organic layers were dried and concentrated in vacuo. The residue was purified using preparative TLC eluting with ethyl acetate to afford the title compound 52 mg (46%). 1H-NMR (CDCl3, 500 MHz): 2.48 (s, 3H), 3.88 (s, 3H), 6.70 (d, J=0.95 Hz, 1H), 7.09 (d, J=7.88 Hz, 1H), 7.24 (m, 1H), 7.25 (s, 1H), 7.44 (t, J=0.95 Hz, 1H), 7.66 (m, 1H), 8.53 (m, 1H), 8.65 (d, J=0.95 Hz, 1H).

Workup

  1. customthe reaction
  2. temperatureagain heated at 210° C. under microwave irradiation for 60 minutes
  3. washthe solution washed with water (3×10 mL) and brine
  4. filtrationThe aqueous was filtered through Celite
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-edd8a7df3ced4e44a01ea28bab69efdb
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

Loading…