Potassium Carbonate → Ethyl 4-(3-(2-(7-bromoquinolin-2-yl)ethenyl)phenoxy)butyrate

HRID 1088464Notes

Reaction equation

HRID 1088464 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[C:13][C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(C(C)=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=3)[O:20][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 104714733-(2-(7-Bromoquinolin-2-yl)-ethynyl)phenolHCID 10890062Ethyl 4-iodobutanoate

Product 1

HCID 53654124Ethyl 4-(3-(2-(7-bromoquinolin-2-yl)ethenyl)phenoxy)butyrate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of the phenol from Step 3 (470 mg), methyl ethyl ketone (10 mL), milled potassium carbonate (600 mg) and ethyl 4-iodo-butyrate (421 mg) was refluxed overnight The solids were filtered, and the filtrate was evaporated. The residue was purified by flash chromatography using toluene-ethyl acetate (10:0.3) to afford the title product as yellow solid: m.p. 61°-63° C.

Workup

  1. temperaturewas refluxed overnight The solids
  2. filtrationwere filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b661c84022bc4384aa4bbc3d3c986a02
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

Loading…