Sodium Carbonate → HCID 59570665, compound

HRID 1961710Notes

Reaction equation

HRID 1961710 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[N:12][CH:11]=[C:10](Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH:27]=[CH:26][C:25](B(O)O)=[N:24]1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C.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>[C:1]([O:5][C:6](=[O:22])[N:7]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[N:12][CH:11]=[C:10]([C:27]2[NH:23][N:24]=[CH:25][CH:26]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 59570677(4-Chloro-phenyl)-(6-chloro-pyrazin-2-yl)-carbamic acid tert-butyl esterHCID 178514837HCID 178514837, compound

Product 1

HCID 59570665HCID 59570665, compoundYield 26.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(4-Chloro-phenyl)-(6-chloro-pyrazin-2-yl)-carbamic acid tert-butyl ester (350 mg, 1.03 mmol), 1H-pyrazole-3-boronic acid (128 mg, 1.13 mmol) and sodium carbonate (218 mg, 2.06 mmol) in water (1 mL) and ethanol (4 mL) were degassed with argon for 30 minutes before tetrakis(triphenylphosphine)palladium(0) (59 mg, 0.051 mmol) was added. The reaction mixture was heated to reflux over night. Water was added and the mixture was concentrated in vacuo. The remaining aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic phases were washed with brine, dried over sodium sulphate, filtrated and evaporated. The crude product was purified by column chromatography (ethyl acetate/heptane as eluent) to give (4-chloro-phenyl)-[6-(2H-pyrazol-3-yl)-pyrazin-2-yl]-carbamic acid tert-butyl ester (100 mg, 26%) as a colourless solid.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux over night
  4. concentrationthe mixture was concentrated in vacuo
  5. extractionThe remaining aqueous phase was extracted with ethyl acetate (3×50 mL)
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltrated
  9. customevaporated
  10. customThe crude product was purified by column chromatography (ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-5f6324da807d4bad8951edc7ae120c1f
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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