Cesium carbonate → HCID 11856436, compound

HRID 643300Notes

Reaction equation

HRID 643300 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([CH3:12])=[C:7]2[C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.[CH3:20][O:21][C:22](=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([CH3:12])=[C:7]2[C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C:22]([O:21][CH3:20])=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetateHCID 11856437HCID 11856437, compound

Product 1

HCID 11856436HCID 11856436, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(8-chloro-3-methylcinnolin-4-yl)phenol (0.21 g, 0.78 mmol), 4-bromomethylphenyl acetic acid methyl ester (0.42 g, 1.64 mmol), and cesium carbonate (1.70 g, 5.2 mmol) in acetone (15 mL) was refluxed for 2 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic residue was purified by silica gel chromatography using 5-50% EtOAc/hexanes as eluent to provide the title compound (0.28 g) as a gum. MS (ESI) m/z 433; HRMS (ESI, [M+H]+) 433.1335.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ecd4e8a7280440e28b06c5a5c45a35db
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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