Potassium Carbonate → HCID 71246043, compound

HRID 573983Notes

Reaction equation

HRID 573983 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH2:13]([N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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>[CH2:13]([N:20]1[CH:24]=[C:23]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=2)[CH:22]=[N:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 156456645-Bromo-2-methoxy-3-nitropyridine

Product 1

HCID 71246043HCID 71246043, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried resealable Schlenk tube was charged with 5-bromo-2-methoxy-3-nitropyridine (3.58 g, 15.36 mmol), 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.23 g, 18.43 mmol), potassium carbonate (4.24 g, 30.72 mmol), 1,4-dioxane (50 mL) and water (5 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium(0) (1.77 g, 1.53 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 100° C. After 3 days, the mixture was cooled, filtered through diatomaceous earth (Celite®) and the filter cake was washed with methylene chloride (300 mL). The combined filtrate and washings were concentrated in vacuo and the residue was purified by flash chromatography (20-50% ethyl acetate in hexanes) to give the title compound (3.70 g, 84%) as a yellow solid.

Workup

  1. additionwas added
  2. customAfter three further cycles of evacuation-backfilling with argon, the Schlenk tube was sealed
  3. temperaturethe mixture was cooled
  4. filtrationfiltered through diatomaceous earth (Celite®)
  5. washthe filter cake was washed with methylene chloride (300 mL)
  6. concentrationThe combined filtrate and washings were concentrated in vacuo
  7. customthe residue was purified by flash chromatography (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c5fd10e78a9e45d0b4865f2e92c6866b
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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