Tetrahydrofuran → 5-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820894Notes

Reaction equation

HRID 1820894 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]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].O1CCCC1>C(=O)([O-])[O-].[K+].[K+].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.O.C(OCC)(=O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 27347023,4-Dimethoxyphenylboronic acidHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 101492305-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridineYield 41%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave safe tube, 5-bromo-7-azaindole (81, 392 mg, 1.99 mmol), prepared from 7-azaindole following the published procedure (Marie-Claude, Viaud, Heterocycles, 1999, 50, 1065-1080), 3,4-dimethoxyphenyl boronic acid (905 mg, 4.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.099 mol) were mixed in 1.0 M of potassium carbonate (6.0 mL) and tetrahydrofuran (9.5 mL, 0.12 mol). The resulting mixture was heated at 120° C. in a CEM Discover microwave unit for 10 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:hexanes) to yield the desired product as a light yellow solid (82, 207 mg, 41%). 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:hexanes)

Sources & evidence

ORD record
ord-755c5fc7ffa141e29eaaabaa825a9ce4
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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