Ethyl Acetate → 4-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820892Notes

Reaction equation

HRID 1820892 reaction equation
Cl[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.N1C2C(=CC=CN=2)C=C1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(OCC)(=O)C>C(=O)([O-])[O-].[K+].[K+].O.O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:6][CH:5]=[CH:4][C:3]=23)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 27347023,4-Dimethoxyphenylboronic acidHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 119990244-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave reaction tube, 4-chloro-7-azaindole (49, 1.362 g, 8.926 mmol), prepared from 7-azaindole following published procedure (Schneller, S. W.; Luo, Jiann-Kuan. J. Org. Chem. 1980, 45, 4045-4048), 3,4-dimethoxyphenyl boronic acid (4.06 g, 22.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (52 mg, 0.45 mmol) were mixed in 1.0 M potassium carbonate in water (27 mL) and tetrahydrofuran (43 mL). The resulting mixture was heated at 150° C. in a CEM Discover microwave unit for 20 minutes. Ethyl acetate and water were added, and the two layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded the crude material, which was purified by column chromatography (40-70% ethyl acetate in hexane) to yield the desired product in light yellow solid (50, 974 mg, 3.83 mmol). MS(ESI) [M+H+]+=255.2.

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure
  6. customafforded the crude material, which
  7. customwas purified by column chromatography (40-70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-315f66e012a74002863f089961bf69cc
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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