Pyridine → HCID 86672157, compound

HRID 1842956Notes

Reaction equation

HRID 1842956 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([F:11])[CH:3]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>CC(C)=O>[F:11][C:4]1[CH: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]=[CH:6][C:5]=1[CH2:8][CH2:9][OH:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 450906002-(4-Amino-2-fluorophenyl)ethanol

Product 1

HCID 86672157HCID 86672157, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(4-amino-2-fluorophenyl)ethanol (1.3 g, 8.38 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (1.32 g, 16.7 mmol, 2.0 eq) and phenyl chloroformate (1.45 g, 9.23 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 2 h. The solvent was evaporated, the residue diluted with EtOAc (50 mL), washed with water (100 mL) followed by brine and the solvent evaporated. The resulting residue was purified by CC using EtOAc/PE (1:4) to get phenyl 3-fluoro-4-(2-hydroxyethyl)phenylcarbamate (1.5 g, 65%, white solid). (TLC system: EtOAc/PE (1:1), Rf: 0.3).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with EtOAc (50 mL)
  3. washwashed with water (100 mL)
  4. customthe solvent evaporated
  5. customThe resulting residue was purified by CC

Sources & evidence

ORD record
ord-1a772fdb4e404ab6b95d4cbe5d28175d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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