3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate → N-[4-(3,6-Dihydro-2H-pyran-4-yl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878188Notes

Reaction equation

HRID 878188 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[O:26]1[CH2:31][CH:30]=[C:29](OS(C(F)(F)F)(=O)=O)[CH2:28][CH2:27]1>>[O:26]1[CH2:27][CH:28]=[C:29]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 113567033,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonateHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670777N-[4-(3,6-Dihydro-2H-pyran-4-yl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 73, from N-(4-iodo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 98, intermediate a) and trifluoro-methanesulfonic acid 3,6-dihydro-2H-pyran-4-yl ester (CAS RN 188975-30-6). The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 40:60). Colorless solid (56%). MS (ESI): m/z=431.177 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 40:60)

Sources & evidence

ORD record
ord-00fa3f8205344a738cab6760b7b9b3ce
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…