Pyridine → Phenyl 6-fluoropyridin-3-ylcarbamate

HRID 218310

Reaction equation

HRID 218310 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].CCOC(C)=O>C1COCC1>[F:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 59313675Phenyl 6-fluoropyridin-3-ylcarbamateYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Fluoropyridin-3-amine (224 mg, 2.00 mmol) was dissolved in THF (4 mL). Pyridine (202 μL, 2.50 mmol) was added, followed by phenyl chloroformate (258 μL, 2.06 mmol). The reaction was stirred at rt for 2 h, then EtOAc (20 mL) was added. The reaction was washed with 1 M HCl (10 mL), water (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give slightly impure 16A (471 mg, >100%). 16A had an analytical HPLC retention time=2.437 min (Phenomenex Luna 3.0×50 mm, 10-90% aqueous MeOH over 5 min containing 0.1% TFA) and a LC/MS M++1=233.

Workup

  1. washThe reaction was washed with 1 M HCl (10 mL), water (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45af494887794d2b85dd312bb66f8e4a
Source dataset
uspto-grants-2012_06
Patent number
US08198438B2

Linked notes

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