Acetone → HCID 53805783, compound

HRID 465695Notes

Reaction equation

HRID 465695 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:17]([C:18]#[N:19])=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.[CH2:22](Br)[C:23]#[CH:24].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH2:24][C:23]#[CH:22])=[CH:6][C:5]([N:9]2[C:17]([C:18]#[N:19])=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 19875211HCID 19875211, compound2×

Product 1

HCID 53805783HCID 53805783, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of Example 57, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,3,5,6,7,8-hexahydro-3- oxoimidazo[1,5-a]pyridine-1-carbonitrile (2.6 g, 0.0085 mol) was treated with 1.5 g (0.010 mol) of an 80% solution of propargyl bromide in toluene and 1.4 g (0.01 mol) of potassium carbonate in refluxing acetone, as described in Example 34, to furnish, after recrystallization from ethanol, 2.2 g of 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2,3,5,6,7,8-hexahydro-3-oxoimidazo[1,5-a]pyridine-1-carbonitrile (XXI) (m.p. 166°-8° C.).

Workup

  1. customto furnish
  2. customafter recrystallization from ethanol, 2.2 g of 2-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2,3,5,6,7,8-hexahydro-3-oxoimidazo[1,5-a]pyridine-1-carbonitrile (XXI) (m.p. 166°-8° C.)

Sources & evidence

ORD record
ord-cc92f2041ab842b78ebd8bb3a3098430
Source dataset
uspto-grants-1992_10
Patent number
US05153316

Reaction notes

Loading…