Sodium Carbonate → 3-[2-chloro-6-(2,3-dimethylphenyl)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridine

HRID 2088990Notes

Reaction equation

HRID 2088990 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[CH3:27][C:28]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.C(OCC)(=O)C>[Cl:26][C:4]1[CH:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:7]=[C:2]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([CH3:34])[C:28]=2[CH3:27])[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 866498693-(2,6-dichloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 871915433-[2-chloro-6-(2,3-dimethylphenyl)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridineYield 13.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

To a solution of Example 7a (0.08 g, 0.2 mmol), in 2 mL dimethoxyethane/ethanol/water (7:2:3) was added 2,3-dimethylphenylboronic acid (0.036 g, 0.27 mmol), catalytic dichlorobis(triphenylphosphine) palladium(II) and 0.297 mL of 1M aqueous sodium carbonate. The contents were heated at 150 degrees for 30 minutes in a microwave. The reaction was diluted with ethyl acetate and washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (gradient elution, ethyl acetate/hexane 0-50%). The material obtained (35 mg) after concentration of the fractions was purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm), eluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A) to give 9 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 2.19-2.27 (m, 3H) 2.33 (s, 3H) 6.94-7.53 (m, 4H) 7.80 (d, J=9.52 Hz, 2H) 8.19-8.55 (m, 3H) 12.36 (s, 1H). MS (ESI+) m/z 333.9 (M+H)+.

Workup

  1. temperatureThe contents were heated at 150 degrees for 30 minutes in a microwave
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using flash chromatography (gradient elution, ethyl acetate/hexane 0-50%)
  7. customThe material obtained (35 mg) after concentration of the fractions
  8. customwas purified by preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm×75 mm)
  9. washeluting with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B), at a flow rate of 50 mL/min (0-0.5 min 10% A, 0.5-7.0 min linear gradient 10-95% A, 7.0-10.0 min 95% A, 10.0-12.0 min linear gradient 95-10% A)

Sources & evidence

ORD record
ord-c8916297911b4bec9b0a5b640ae7f68a
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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