Iodine → HCID 67342352, compound

HRID 451471Notes

Reaction equation

HRID 451471 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[N:11]([N:19]=[C:20]([NH2:22])[N:21]=3)[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Mg].II>CO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH:13]([C:15]([F:17])([F:16])[F:18])[CH2:12][N:11]3[N:19]=[C:20]([NH2:22])[N:21]=[C:10]23)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 807IodineHCID 5462224MagnesiumHCID 67334012HCID 67334012, compound

Product 1

HCID 67342352HCID 67342352, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(3,4-difluorophenyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (500 mg, 1.59 mmol) and magnesium (309 mg, 12.7 mmol) in methanol (80 mL) and THF (40 mL) was added iodine (2 mg, 7.88 μmol), stirred for 10 minutes at room temperature, then sonicated for 30 minutes. The reaction mixture was concentrated in vacuo. The residue was dissolved in THF and dried over Na2SO4, then filtered off, washed thoroughly with THF and the solvents were evaporated. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as mixture of racemic diastereomers as white solid (324 mg, 64%).

Workup

  1. customsonicated for 30 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in THF
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered off
  6. washwashed thoroughly with THF
  7. customthe solvents were evaporated
  8. customThe crude material was purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane)

Sources & evidence

ORD record
ord-6a0ff51011724b709e21b14798fa7d6c
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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