Pyridine → Isopropenyl [4-(trifluoromethyl)pyridin-2-yl]carbamate

HRID 1091512Notes

Reaction equation

HRID 1091512 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]([CH3:24])=[CH2:23])=[O:20]>C1COCC1>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:19](=[O:20])[O:21][C:22]([CH3:24])=[CH2:23])[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 93846Isopropenyl chloroformateHCID 27783152-Amino-4-(trifluoromethyl)pyridine

Product 1

HCID 59232120Isopropenyl [4-(trifluoromethyl)pyridin-2-yl]carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(trifluoromethyl)pyridin-2-amine (1.0 g, 6.17 mmol) was dissolved in THF (20 mL) and treated with pyridine (600 μL, 7.4 mmol) and isopropenyl chloroformate (596 μL, 6.17 mmol). The reaction was stirred at rt for 6 h. The reaction was then concentrated and triturated with EtOAc. The crude residue was purified by MPLC (100% CH2Cl2) to yield a pale yellow solid (1.2 g, 79%); 1H-NMR (DMSO-d6) δ 11.0 (s, 1H), 8.57 (d, J=5.1 Hz, 1H), 8.10 (s, 1H), 7.45 (d, J=5.5 Hz, 1H), 4.81 (t, J=1.1 Hz, 1H), 4.76 (s, 1H), 1.94 (s, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. customtriturated with EtOAc
  3. customThe crude residue was purified by MPLC (100% CH2Cl2)

Sources & evidence

ORD record
ord-a8ce4727b8ed415290a375d2e729588d
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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