Lithium Hydroxide → HCID 71295159, compound

HRID 1776915Notes

Reaction equation

HRID 1776915 reaction equation
[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([O:19]CC)=[O:18])[C:6]=2[CH:22]=1.[Li+].[OH-]>O1CCOCC1.O>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][CH2:25][C:24]2=[O:28])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([OH:19])=[O:18])[C:6]=2[CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71295154HCID 71295154, compound

Product 1

HCID 71295159HCID 71295159, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl 5-bromo-2-(4-fluorophenyl)-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxylate (2.5 g, 5.8 mmol) and LiOH (0.5 g, 21.0 mmol) in dioxane (30 mL) and water (10 mL) was allowed to stir at 90° C. for 1 hour. The mixture was cooled to room temperature and extracted with dichloromethane, the organic extract was washed with brine, dried over Na2SO4 and concentrated to provide 5-bromo-2-(4-fluorophenyl)-6-(2-oxopyrrolidin-1-yl)benzofuran-3-carboxylic acid (2.2 g, yield: 91%). 1H-NMR (CDCl3, 400 MHz) δ 8.08 (s, 1H), 7.81˜7.84 (m, 2H), 7.34 (s, 1H), 6.89˜6.93 (m, 2H), 3.79˜3.82 (m, 2H), 2.66˜2.70 (m, 2H), 2.26˜2.31 (m, 2H). MS (M+H)+: 418/420.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with dichloromethane
  3. extractionthe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9cbcd8b8c6934635990173d3b5f58716
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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