Tetrahydrofuran → 5-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

HRID 1024255Notes

Reaction equation

HRID 1024255 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.O1CCCC1.[CH3:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1>C(=O)([O-])[O-].[K+].[K+].O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.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>[CH3:16][N:17]1[CH:21]=[C:20]([C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)[CH:19]=[N:18]1

Participants

8

Reactant 3

HCID 8028TetrahydrofuranHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To 5-bromo-7-azaindole (44, 1.04 g, 5.28 mmol) in 1.00M potassium carbonate in water (15.8 mL) and tetrahydrofuran (50.0 mL) were added 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (546, 1.65 g, 7.92 mmol), Tetrakis(triphenylphosphine)palladium(0) (0.305 mg, 0.26 mmol) and tetra-n-butylammonium iodide (0.20 g, 0.53 mmol). The reaction mixture was stirred at 70° C. overnight. The reaction mixture was poured into water and the organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified with silica gel column chromatography eluting with 25% ethyl acetate in hexane to provide a light yellow solid (547, 670 mg, 64.0%). MS (ESI)[M+H+]+=199.4.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel column chromatography
  5. washeluting with 25% ethyl acetate in hexane
  6. customto provide a light yellow solid (547, 670 mg, 64.0%)

Sources & evidence

ORD record
ord-085298d436b24749b8153d4ffe78c0ff
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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