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

HRID 1367367Notes

Reaction equation

HRID 1367367 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 1.00 M 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-655e499262f148b4b2984bf347b174ea
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

Loading…