Sodium Carbonate → 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropanenitrile

HRID 1920840Notes

Reaction equation

HRID 1920840 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[CH3:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=1)([CH3:15])[C:13]#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[NH:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([C:18]3[CH:17]=[C:16]([C:12]([CH3:15])([CH3:11])[C:13]#[N:14])[CH:21]=[CH:20][CH:19]=3)=[C:3]2[CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridineHCID 579697952-Methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile

Product 1

HCID 426348322-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropanenitrileYield 53.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 4-iodo-1H-pyrazolo[3,4-b]pyridine (50 mg, 0.204 mmol), 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (66 mg, 0.245 mmol), 2 M aqueous solution of sodium carbonate (0.31 ml, 0.612 mmol), tetrakis(triphenylphosphine)palladium(0) (5 mol %, 12 mg, 0.01 mmol), in ethylene glycol dimethyl ether (2.5 ml) was heated under microwave irradiation at 150° C. for 30 minutes. The mixture was cooled down to room temperature, filtered through a path of celite and evaporated to dryness. The residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (28.4 mg, 53% yield).

Workup

  1. filtrationfiltered through a path of celite
  2. customevaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-fb9d0cd6384d4460b53ff906d843d5db
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

Loading…