Sodium Carbonate → HCID 21866208, compound

HRID 857737Notes

Reaction equation

HRID 857737 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O)=[O:15]>COCCOC.O.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>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:14]=[O:15]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 73277ChloropyrazineHCID 2921892-Formylphenylboronic acid

Product 1

HCID 21866208HCID 21866208, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of Pd(PPh3)4 (330 mg, 0.28 mmol) and chloropyrazine (987 μL, 11.0 mmol) in anhydrous DME (60 mL) was stirred for 20 min at room temperature under N2 atmosphere. The resulting red-orange mixture was treated with a solution of Na2CO3 (1.05 mg, 3.30 mmol) in H2O (15 ml), followed by 2-formylbenzene boronic acid (1.50 mg, 9.90 mmol), resulting in a white precipitate. The mixture was heated to reflux for 1.5 h. The DME was then removed in vacuo and the residual suspension was extracted twice with CH2Cl2. The combined organic extracts were dried (anhydrous Na2SO4) and concentrated to give the title compound as a red-orange solid which was dried in vacuo for 16 h and used without further purification. LCMS (M+H): 185.02.

Workup

  1. customresulting in a white precipitate
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1.5 h
  4. customThe DME was then removed in vacuo
  5. extractionthe residual suspension was extracted twice with CH2Cl2
  6. dry with materialThe combined organic extracts were dried (anhydrous Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef314fc3b01c46fbbe1f2cd65ee209fe
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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