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Isoamyl Nitrite → 5-Bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester

HRID 416470
Notes
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Reaction equation

HRID 416470 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9][C:8](N)=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:6]=1)=[O:4].C(ON=O)CC(C)C.C[Si](C)(C)[Br:33].C(=O)(O)[O-].[Na+]>BrCBr>[CH3:1][O:2][C:3]([C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9][C:8]([Br:33])=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:6]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8053Isoamyl Nitrite2×HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 666225955-Amino-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 866347025-Bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 3024DibromomethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2.11 g 5-amino-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester in 20 ml dibromomethane was added 1.59 g isoamylnitrite and the mixture was cooled to 0° C. To the resulting suspension was added 2.922 g trimethylbromosilane and the mixture was stirred at 0° C. for 10 min (no conversion by HPLC) and at room temperature for 3 h. To the dark reaction mixture was added another 1.59 g isoamylnitrite and the mixture was stirred at room temperature for 6 h. The dark reaction mixture was pored onto ice and ca 20 ml 10% sodium bicarbonate and the product was extracted with dichloromethane (2.64 g raw material which crystallized) and purified by chromatography on silica gel (20 g hep:EE=9:1 to 1:1) to yield 2.290 g of the title compound as white crystals. MS (M+H at 396.8 and 394.9).

Workup

  1. customTo the dark reaction mixture
  2. stirringthe mixture was stirred at room temperature for 6 h
  3. customThe dark reaction mixture
  4. extractionthe product was extracted with dichloromethane (2.64 g raw material which crystallized)
  5. custompurified by chromatography on silica gel (20 g hep:EE=9:1 to 1:1)

Sources & evidence

ORD record
ord-0a8c97580b204972bd1e313ca2a6edab
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088920B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes