Acetic Acid → (+/-)-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

HRID 857340Notes

Reaction equation

HRID 857340 reaction equation
[Br:1][C:2]1[C:3]2[CH:4]=[C:5]3[CH:14]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1.C1COCC1.CO.[Li+].[OH-].CC(O)=O>[Cl-].[Na+].O>[Br:1][C:2]1[C:3]2[CH:4]=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 11267347Methyl 2-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 21867415(+/-)-(8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (+/−)-methyl (8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (11 g) in a THF/MeOH (3:1) mixture at r.t. was added 1N LiOH (50 mL, aqueous solution). The reaction mixture was stirred at r.t. for 12 hours and AcOH (5 mL) and brine (100 mL) were added. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated to provide the title compound as a white solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8deef22c67f049a2ae7a66dae9745aab
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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