Ethyl 2-amino-4-(4-bromophenyl)thiophene-3-carboxylate → 4-(4-Bromo-phenyl)-2-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid ethyl ester

HRID 1244166Notes

Reaction equation

HRID 1244166 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:18])=[O:5])[CH3:2].Cl[CH:20]([C:26]([O-])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH:18][C:26](=[O:27])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 727636Ethyl 2-amino-4-(4-bromophenyl)thiophene-3-carboxylateHCID 86592122Monoethyl chloromalonate

Product 1

HCID 696073284-(4-Bromo-phenyl)-2-(2-ethoxycarbonyl-acetylamino)-thiophene-3-carboxylic acid ethyl esterYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-(4-bromophenyl)-thiophene-3-carboxylic acid ethyl ester (4.00 g, 11.5 mmol) in CH2Cl2 (40 mL) was added ethyl chloromalonate (2.15 g, 14.2 mmol) slowly. The mixture was then heated to reflux for 30 min. The mixture was concentrated under reduced pressure and separated by flash chromatography on silica gel (5–30% ethyl acetate in hexanes) giving the titled compound (4.98 g, 98.5%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 30 min
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customseparated by flash chromatography on silica gel (5–30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fa29ac6a4ce445688c0feff8a8bbaebf
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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