HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetonitrile → Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 24250
Notes
Print preview

Reaction equation

HRID 24250 reaction equation
BrCC1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1C(C)C.[C:25]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=O)[CH3:26].[C:33]([O-])([O-])=O.[Na+].[Na+].[CH3:39][C:40]#N>O>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]#[C:9][C:6]2[CH:5]=[CH:4][C:25]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[C:26]([CH:40]([CH3:39])[CH3:33])[C:7]=2[CH3:8])=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 86585936Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate2×

Product 1

HCID 86585935Methyl [4-(4-imidazol-1-yl-methyl-3-isopropyl-phenylethynyl)-phenyl]-acetateYield 58%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Procedure

A solution of methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Intermediate 156, 72.0 mg, 0.19 mmol) and 1-acetylimidazole (22.0 mg, 0.20 mmol) in 5 mL CH3CN was heated at 65° C. for 8 h and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (0.5% Et3N in 5% MeOH-EtOAc) afforded 40.0 mg (58%) of the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c5327f06f7443058d402b085009dedf
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855512B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes