Potassium Carbonate → HCID 58966923, compound

HRID 1948218Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:20])=[C:4]([F:23])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]#[N:33]>C(#N)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:8](=[O:20])[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:31][C:32]#[N:33])=[CH:15][CH:14]=3)=[CH:12]2)=[C:4]([F:23])[CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

According to Scheme 14 Method A: A suspension of 1-(4-chloro-2-fluorobenzyl)-5-(4-hydroxyphenyl)pyridin-2(1H)-one (1 eq, 1.21 mmol, 0.40 g), K2CO3 (10 eq, 12.1 mmol, 1.68 g) and 2-bromoacetonitrile (1 eq, 1.21 mmol, 0.15 g) in acetonitrile (10 mL) was heated in a microwave at 180° C. during 5 min. The reaction mixture was filtered, the filtrate was concentrated and the resulting crude residue was dissolved in CH2Cl2. The organic phase washed with water, dried over MgSO4, filtered and evaporated. The crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 98/2 as eluent followed by trituration in acetonitrile to afford 2-(4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetonitrile (0.51 mmol, 0.19 g, 42%) as a white solid.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
dissolutionthe resulting crude residue was dissolved in CH2Cl2
washThe organic phase washed with water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record: ord-8d5064f87c664e88b49877ee0a4c077d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399493B2

Reaction notes

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