Pyridine → 6-Bromo-4-methyl-beta-carbolin-3-carboxylic acid ethyl ester

HRID 1085442Notes

Reaction equation

HRID 1085442 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].N1C=CC=CC=1.[Br:26]Br>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([Br:26])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 12795657HCID 12795657, compound

Product 1

HCID 130373286-Bromo-4-methyl-beta-carbolin-3-carboxylic acid ethyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

0.5 g of 4-methyl-β-carbolin-3-carboxylic acid ethyl ester (melting point 235°-239° C.) is dissolved in 25 ml of chloroform and 1.7 ml of pyridine and a solution of 1 ml of bromine in 21 ml of chloroform is added dropwise thereto at 0° C. After standing for one hour while cooling with ice and after dilution with 50 ml of methylene chloride, the mixture is extracted by washing with sodium thiosulphate solution, dilute aqueous ammonia solution and water. After drying with sodium sulphate, filtering off and distilling off the solvent in vacuo, 6-bromo-4-methyl-β-carbolin-3-carboxylic acid ethyl ester is obtained in 38% yield, Melting point 231°-232° C. (from acetone).

Workup

  1. customat 0° C
  2. temperaturewhile cooling with ice
  3. extractionafter dilution with 50 ml of methylene chloride, the mixture is extracted
  4. washby washing with sodium thiosulphate solution, dilute aqueous ammonia solution and water
  5. dry with materialAfter drying with sodium sulphate
  6. filtrationfiltering off
  7. distillationdistilling off the solvent in vacuo

Sources & evidence

ORD record
ord-d6548a814f9c4e7eb4ddf7c88e859734
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

Loading…