1,2-Dimethoxyethane → HCID 117770786, compound

HRID 1526371Notes

Reaction equation

HRID 1526371 reaction equation
Br[C:2]1[C:3]([O:16][CH3:17])=[C:4]([C:14]#[N:15])[C:5](=[O:13])[N:6]([CH:8]([CH:10]2[CH2:12][CH2:11]2)[CH3:9])[CH:7]=1.[CH3:18][N:19]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[N:20]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.O>[CH:10]1([CH:8]([N:6]2[CH:7]=[C:2]([C:21]3[CH:22]=[CH:23][N:19]([CH3:18])[N:20]=3)[C:3]([O:16][CH3:17])=[C:4]([C:14]#[N:15])[C:5]2=[O:13])[CH3:9])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27600771-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 117769989HCID 117769989, compound

Product 1

HCID 117770786HCID 117770786, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-1-(1-cyclopropylethyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step B of Example 163 (66 mg), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (69 mg), tetrakis(triphenylphosphine)palladium(0) (26 mg), aqueous sodium carbonate solution (2 M, 0.666 mL) and 1,2-dimethoxyethane (3.0 mL) was heated with microwave irradiation at 100° C. for 1 hr under argon atmosphere. The reaction mixture was cooled to room temperature, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and then silica gel column chromatography (basic silica gel, hexane/ethyl acetate) to give the title compound (26 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76487b5e23814f6cbd9f5dc70fa0f862
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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