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Aniline → HCID 61699136, compound

HRID 333533
Notes
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Reaction equation

HRID 333533 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[C:10]([Cl:15])=[N:11][CH:12]=[CH:13][N:14]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:15][C:10]1[C:9]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:14][CH:13]=[CH:12][N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6115AnilineHCID 785752,3-DichloropyrazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 61699136HCID 61699136, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Aniline (11.25 g, 121 mmol), dichloropyrazine (20 g, 134 mmol), sodium t-butoxide (15.48 g, 161 mmol) were stirred in toluene (300 mL) under nitrogen purging for 15 minutes. Pd2(dba)3 (1.23 g, 1.34 mmol) and BINAP (3.34 g, 5.47 mmol) were added. The reaction was heated to 90° C. for 5 h. After it cooled to room temperature, the reaction was filtered through Celite®. After solvent evaporation, the residue was purified with column chromatography using 30% ethyl acetate in hexanes as solvent to give 3-chloro-N-phenylpyrazin-2-amine (4.5 g, 16.3% yield).

Workup

  1. temperatureAfter it cooled to room temperature
  2. filtrationthe reaction was filtered through Celite®
  3. customAfter solvent evaporation
  4. customthe residue was purified with column chromatography

Sources & evidence

ORD record
ord-c481bd70eae74b56bab4250f5a898d35
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883322B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes