Pyridine → Ethyl 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionate

HRID 238922Notes

Reaction equation

HRID 238922 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:13].[CH3:14][S:15](Cl)(=[O:17])=[O:16].N1C=CC=[CH:21][CH:20]=1>>[F:13][C:3]1[CH:4]=[C:5]([CH:8]([CH3:12])[C:9]([O:11][CH2:20][CH3:21])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 866091712-(4-Amino-3-fluorophenyl)propionate

Product 1

HCID 24754385Ethyl 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionateYield 91%

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4-amino-3-fluorophenyl)propionate (1-13, 4 mM) and pyridine (10 ml) was dissoluted with methansulfonylchloride (6 mM) and was stirred at 0° C. for 10 minutes. The combined organic layers were washed with H2O and residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:2) as eluant to afford ethyl 2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionate compound (1-26, SU-658).

Workup

  1. washThe combined organic layers were washed with H2O and residue
  2. customwas purified by flash column chromatography on silica gel with EtOAc/hexanes (1:2) as eluant

Sources & evidence

ORD record
ord-116ba5f3ec5347fcaaf9cd8bda8012b5
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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