Sodium Hydroxide → 4-Bromo-3-cyano-5-ethyl-1H-pyrrole-2-carboxylic acid

HRID 2233831Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.C[O:10][C:11]([C:13]1[NH:14][C:15]([CH2:20][CH3:21])=[CH:16][C:17]=1[C:18]#[N:19])=[O:12].[OH-].[Na+]>C(Cl)Cl>[Br:1][C:16]1[C:17]([C:18]#[N:19])=[C:13]([C:11]([OH:10])=[O:12])[NH:14][C:15]=1[CH2:20][CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

N-Bromosuccinimide (289 mg, 1.63 mmol) was added to a cooled solution of 3-cyano-5-ethyl-1H-pyrrole-2-carboxylic acid methyl ester (Intermediate 27; 290 mg, 1.63 mmol) in anhydrous DCM at 0° C. The mixture was stirred at 0° C. for 30 minutes. The mixture was poured into a cold solution of 2 N sodium hydroxide (15 ml) and extracted with DCM. The combined extracts were washed with water (2×15 ml), dried over sodium sulphate and concentrated in vacuo to give small amounts of title compound. The aqueous phase was acidified, extracted with EtOAc, concentrated in vacuo to give the title compound as a creamy brown solid (240 mg).

Workup

extractionextracted with DCM
washThe combined extracts were washed with water (2×15 ml)
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8dc104e1ebf14d2794818aff45ecc173
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

Loading…