Pyridine → HCID 59394204, compound

HRID 1971336Notes

Reaction equation

HRID 1971336 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C1COCC1.C(Cl)Cl>[C:22]1([O:21][C:19](=[O:20])[NH:9][C:5]2[CH:6]=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 140519365-(Trifluoromethyl)pyridin-3-amine

Product 1

HCID 59394204HCID 59394204, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Example 7-A, 5-trifluoromethyl-pyridin-3-ylamine, (385 mg, 2.37 mmol) is taken up in THF (25 mL) and pyridine (0.38 mL, 4.75 mmol) at 0° C. before phenyl chloroformate (558 mg, 3.56 mmol) is added. After 2 h, the reaction is diluted with DCM (50 mL) and washed with water (50 mL). The organic layer is separated, dried over anhydrous Na2SO4, filtered and concentrated. The residue is then separated via FCC (EtOAc/heptanes 1:9 to EtOAc/heptanes 1:1) to give the title compound. MS (ESI) m/z 283.0 (M+1).

Workup

  1. washwashed with water (50 mL)
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is then separated via FCC (EtOAc/heptanes 1:9 to EtOAc/heptanes 1:1)

Sources & evidence

ORD record
ord-07865cdd392a49e5ac781c2ea79f5363
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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