Potassium Carbonate → Phenyl (4-(trifluoromethyl)pyridin-2-yl)carbamate

HRID 631447Notes

Reaction equation

HRID 631447 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>O1CCCC1>[F:10][C:8]([F:9])([F:11])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 27783152-Amino-4-(trifluoromethyl)pyridine

Product 1

HCID 57955188Phenyl (4-(trifluoromethyl)pyridin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure described in Example 113B, 2-amino-4-trifluoromethylpyridine (462 mg, 2.85 mmoles) was dissolved in 20 ml of tetrahydrofuran. To this solution was added potassium carbonate (511 mgs, 3.7 mmoles) followed by phenyl chloroformate (521 mgs, 3.33 mmoles). The mixture was concentrated and purified according to the procedure in in Example 138 to afford phenyl 4-(trifluoromethyl)pyridin-2-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 9.53 (s, 1H), 8.56 (m, 1H), 8.38 (s, 1H), 7.6-7.4 (m, 2H), 7.3-7.2 (m, 2H), 6.8 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-db4e64149bd04df4b87e88d1e929c252
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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