Water → HCID 58778971, compound

HRID 1372685Notes

Reaction equation

HRID 1372685 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=1[Br:24].[CH3:25][CH2:26]N=C=NCCCN(C)C.Cl.O>CN(C=O)C>[Br:24][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([O:23][CH2:25][CH3:26])=[O:22])[CH:18]=[CH:19][C:14]=1[NH:13][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 69867Indole-3-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20303490(4-Amino-3-bromophenyl)acetic acid

Product 1

HCID 58778971HCID 58778971, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (20 ml) were dissolved indole-3-carboxylic acid (1.00 g, 6.21 mmol) and 4-amino-3-bromophenylacetic acid (1.60 g, 6.21 mmol). To the resulting solution was added EDC HCl (1.43 g, 7.45 mmol) under stirring at room temperature. After the reaction mixture was stirred at room temperature for 4 hours, water was added thereto, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, ethyl (3-bromo-4-((3-indolylcarbonyl)amino)phenyl)acetate (664 mg, 27%) was obtained as a pale yellow solid.

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 4 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions

Sources & evidence

ORD record
ord-c52d80bf0fa64dc7a6edc664b9ecedf1
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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