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

HRID 1820878Notes

Reaction equation

HRID 1820878 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10](Br)=[CH:9]1)=O)(C)(C)C.O1CCCC1.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32].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>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:8][CH:9]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 21669154tert-Butyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Into a round bottom flask was added 3-Bromo-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (6, 2.8 g, 9.4 mmol) and tetrahydrofuran (100 mL). Tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.50 mmol), 3,4-dimethoxyphenylboronic acid (2.1 g, 11 mmol) and 1 M K2CO3 solution (50 mL) The reaction mixture was stirred at 65° C. overnight. The reaction mixture was poured into water and extracted into ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The crude material was purified by column chromatography (gradient system of hexanes and ethyl acetate) to yield the titled compound, 1, (500 mg, 2 mmol, 20%) and 3-(3,4-dimethoxy-phenyl)-pyrrolo[2,4-b]pyridine-1-carboxylic acid tert-butyl ester (2.1 g, 5.9 mmol, 63%). The later compound can be easily converted to the desired compound, 1 by treatment with acid reagents such as TFA or HCl.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe crude material was purified by column chromatography (gradient system of hexanes and ethyl acetate)

Sources & evidence

ORD record
ord-12633798c82645d6b54a11703dbc0575
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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