Isobutylene oxide → 5-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-furo[2,3-c]pyridine

HRID 1471769Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

1,1-Dimethyloxirane (55 μL) is added to a solution of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (0.15 g) in methanol (2 mL) and dichloromethane (3 mL) at room temperature. The solution is stirred at 50° C. overnight. The solution is concentrated to give the crude title compound that is used without further purification. LC (method 4): tR=0.98 min; Mass spectrum (ESI+): m/z=447 [M+H]+.

Workup

concentrationThe solution is concentrated

Sources & evidence

ORD record: ord-7806fb0d48b04b89b86de97677c45319
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012456B2

Reaction notes

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