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Trifluoroacetic acid → Methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate

HRID 1259328
Notes
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Reaction equation

HRID 1259328 reaction equation
[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:4](=[O:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O.[I:30]N1C(=O)CCC1=O.[Al]>O.C(Cl)Cl>[I:30][C:7]1[N:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[C:4](=[O:12])[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[C:2]=1[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 58432791AZ-32S-methyl-ester

Product 1

HCID 66738777Methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylateYield 46%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

Methyl 5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (1.5 g, 4.8 mmol), dry DCM (7.0 mL), trifluoroacetic acid (3.0 mL) and N-iodosuccinimide (1.0 g, 4.5 mmol) were mixed and stirred at RT in the dark (flask covered with aluminum foil). After 5 h, water (5 mL) was added and the mixture was concentrated by rotary evaporation. Water (3 mL) was added once more and the mixture was concentrated as described above. The resulting mixture was diluted with acetonitrile to a total volume of 50 mL. Purification by preparative HPLC with acetonitrile-water as eluent (neutral eluent) gave methyl 6-iodo-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.905 g, 46%) as a yellow crystalline solid.

Workup

  1. concentrationthe mixture was concentrated by rotary evaporation
  2. additionWater (3 mL) was added once more
  3. concentrationthe mixture was concentrated
  4. additionThe resulting mixture was diluted with acetonitrile to a total volume of 50 mL
  5. customPurification by preparative HPLC with acetonitrile-water as eluent (neutral eluent)

Sources & evidence

ORD record
ord-8013738c384b4475972c89694974ab64
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466284B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes