Sodium Carbonate → 2-hydroxyimino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester

HRID 2104212Notes

Reaction equation

HRID 2104212 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C:5](=[N:8][OH:9])[CH2:6]Br)[CH3:2].[Br:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:10])[C:5](=[N:8][OH:9])[CH2:6][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([Br:11])[CH:13]=2)[NH:17][CH:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 249055-BromoindoleHCID 53428735Ethyl 3-bromo-2-(hydroxyimino)propanoate

Product 1

HCID 578059932-hydroxyimino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-bromo-2-hydroxyimino-propionic acid ethyl ester (3.21 g, 15.3 mmol) in CH2Cl2 (20 mL) was slowly added dropwise to a stirring mixture of 5-bromoindole (3.0 g, 15.3 mmol) and Na2CO3 (8.92 g, 84.2 mmol) in CH2Cl2 (30 mL) at room temperature. The mixture was stirred for 20 hours, filtered through CELITE® and concentrated to give 4.94 g of the title compound as a crude material. LCMS m/z (ESI) [M+H]+ calcd for C1-3H14BrN2O3 (Br79) 325.2, found 325.2.

Workup

  1. filtrationfiltered through CELITE®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b4700f65b2b34535a07f4c22f0905805
Source dataset
uspto-grants-2009_08
Patent number
US07576222B2

Reaction notes

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