2-Bromopyridine → HCID 86706326, compound

HRID 2205938Notes

Reaction equation

HRID 2205938 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][CH:21]=[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][CH:21]=[CH:20][N:19]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 867062766-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86706326HCID 86706326, compoundYield 48%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
180 °C

Procedure

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 27 mg 0.10 mmole) and 2-bromopyridine (24 mg, 15 uL, 0.15 mmole) were dissolved in DMA (0.7 ml) and potassium carbonate (20 mg, 0.14 mmole) and copper(I) iodide (4.0 mg, 0.022 mmole) were added. The reaction was placed under argon and heated by microwave at 180° C. for 60 minutes followed by 210° C. for 45 minutes. The reaction was taken up in ethyl acetate (25 mL) and the solution washed with water (3×7 mL) and brine. The aqueous solutions were backwashed with a single portion of ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified using preparative TLC eluting with ethyl acetate to afford the title compound 17 mg (48%). 1H-NMR (CDCl3, 500 MHz): 3.88 (s, 3H), 6.72 (d, J=0.95 Hz, 1H), 7.18 (d of t, J=0.95, 7.88 Hz, 1H), 7.24 (s, 1H), 7.26 (d, J=0.63 Hz, 1H), 7.44 (ddd, J=0.95, 4.73, 7.57 Hz, 1H), 7.51 (t, J=0.95 Hz, 1H), 7.86 (t of d, J=1.89, 7.57 Hz, 1H), 8.66 (d, J=0.95 Hz, 1H), 8.73 (ddd, J=0.95, 1.89, 4.73 Hz, 1H).

Workup

  1. washthe solution washed with water (3×7 mL) and brine
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b296039eaff84e97916727f7dedd87ba
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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