1,2-Dimethoxyethane → HCID 65646516, compound

HRID 1848089Notes

Reaction equation

HRID 1848089 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:8][C:7]1[C:2]([C:13]2[CH:12]=[N:11][N:10]([CH3:9])[CH:14]=2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 785752,3-DichloropyrazineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 65646516HCID 65646516, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 2,3-dichloropyrazine (1.12 g, 7.52 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.56 g, 7.52 mmol), bis(triphenylphosphine)palladium(II) dichloride (270 mg, 0.38 mmol), and Na2CO3 (2.4 g, 22.56 mmol) in a pressure tube were added 1,2-dimethoxyethane (15 mL) and water (2 mL). The flask was evacuated and flushed with argon (3×) and then sealed and heated at 90° C. overnight. The mixture was concentrated under reduced pressure and purified by silica gel chromatography eluting with 20-100% EtOAc/hexanes to afford 2-chloro-3-(1-methyl-1H-pyrazol-4-yl)pyrazine (780 mg, 53%). LCMS (ESI) m/z 195 (M+H)+.

Workup

  1. customThe flask was evacuated
  2. customflushed with argon (3×)
  3. customsealed
  4. concentrationThe mixture was concentrated under reduced pressure
  5. custompurified by silica gel chromatography
  6. washeluting with 20-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-9238f0e36b8e41489912dcea78ed4be9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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