Pyridine → HCID 57656832, compound

HRID 603170

Reaction equation

HRID 603170 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[C:19]([F:22])([F:21])[F:20])[NH2:15].N1C=CC=CC=1>C1COCC1.C(OCC)(=O)C.Cl>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:17][C:18]=1[C:19]([F:21])([F:22])[F:20]

Participants

7

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 679623-Chloro-4-(trifluoromethyl)aniline

Product 1

HCID 57656832HCID 57656832, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl chloroformate (0.86 mL) was added slowly to a stirring solution of 3-chloro-4-trifluoromethyl aniline (933 mg) in THF (10 mL) containing pyridine (1.07 mL) under an argon atmosphere. The reaction was stirred for 18 h then diluted with ethyl acetate (35 mL) and 1M HCl (20 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 then dried (MgSO4), filtered and evaporated. Trituration with 1:9 EtOAc:isohexanes (10 mL) at reflux followed by cooling to RT afforded a solid which was filtered to afford 1.15 g of the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. temperatureTrituration with 1:9 EtOAc:isohexanes (10 mL) at reflux
  7. customafforded a solid which
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-38f70e8d280643899a052228c14cb32f
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Linked notes

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