Phenyl chloroformate → Phenyl [5-(trifluoromethyl)pyridin-2-yl]carbamate

HRID 229628Notes

Reaction equation

HRID 229628 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.C(N(CC)C(C)C)(C)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>C(Cl)Cl.CCOC(C)=O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 11426042Phenyl [5-(trifluoromethyl)pyridin-2-yl]carbamateYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5-(trifluoromethyl)pyridin-2-amine (100 mg, 0.617 mmol) and N,N-diisopropylethylamine (159.5 mg, 215 μL, 1.234 mmol) in 5 mL CH2Cl2 was treated with phenyl chloroformate (106 mg, 85 μL, 0.68 mmol) and left to stir for 3 h at rt. Solution was diluted with EtOAc and washed twice with 1 N HCl and 1 time with brine. The organic layer was dried (Na2SO4) and concentrated to provide a white solid. Tituration with 10% EtOAc in hexanes gave 120 mg (69%, 0.42 mmol) of the above compound as a white solid. 1H-NMR (DMSO-d6) δ 11.26 (s, 1H), 8.70 (s, 1H), 8.22 to 8.16 (m, 1H), 7.99 (d, J=8 Hz, 1H), 7.45 to 7.40 (m, 2H), 7.30 to 7.20 (m, 3 H)

Workup

  1. waitleft
  2. washwashed twice with 1 N HCl and 1 time with brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customto provide a white solid

Sources & evidence

ORD record
ord-3c7d499c08d841318de2a40a6ffa1098
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

Loading…