Sodium Carbonate → HCID 42635199, compound

HRID 384055Notes

Reaction equation

HRID 384055 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[Br:11][C:12]1[CH:13]=[C:14]([C:27]([CH3:31])([CH3:30])[C:28]#[N:29])[CH:15]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:17]=1.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>[Br:11][C:12]1[CH:13]=[C:14]([C:27]([CH3:31])([CH3:30])[C:28]#[N:29])[CH:15]=[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][N:9]=[CH:10][C:3]=23)[CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridineHCID 579696333-Bromo-α,α-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetonitrile

Product 1

HCID 42635199HCID 42635199, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 4-iodo-1H-pyrazolo[3,4-b]pyridine (116 mg, 0.47 mmol), 2-(3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-methylpropanenitrile (137 mg, 0.39 mmol), 2 M aqueous solution of sodium carbonate (0.79 ml, 1.58 mmol), tetrakis(triphenylphosphine)palladium(0) (5 mol %, 23 mg, 0.02 mmol), in ethylene glycol dimethyl ether (4 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 (102.5 mg, 77% 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-c35fc8fb568d4560afd34fc006b685d6
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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