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

HRID 1099310Notes

Reaction equation

HRID 1099310 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, 1 H), 8.57 (d, J=5.1 Hz, 1H), 8.10 (s, 1 H), 7.45 (d, J=5.5 Hz, 1 H), 4.81 (t, J=1.1 Hz, 1H), 4.76 (s, 1 H), 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-915e218e95154621a30acd604d1c4887
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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