Lithium Hydroxide → 7-bromo-5-fluoro-1H-indole-2-carboxylic acid

HRID 415044

Reaction equation

HRID 415044 reaction equation
O1CCCC1.[OH-].[Li+].C([O:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[Br:23])=[O:12])C>O>[Br:23][C:16]1[CH:17]=[C:18]([F:22])[CH:19]=[C:20]2[C:15]=1[NH:14][C:13]([C:11]([OH:12])=[O:10])=[CH:21]2

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21014457Ethyl 7-bromo-5-fluoro-1H-indole-2-carboxylate

Product 1

HCID 219043557-bromo-5-fluoro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrahydrofuran (35.2 ml), water (23.5 ml), lithium hydroxide (2.61 g, 10.9 mmol), and 7-bromo-5-fluoro-1H-indole-2-carboxylic acid ethyl ester (3.11 g, 10.9 mmol) were added to a round bottom flask and mixed with a magnetic stirrer. This mixture was refluxed for 1 hour. The THF was removed via rotary evaporator, and the aqueous solution was acidified with 1M HCL, and extracted with ethyl acetate. 1H NMR (DMSO-d6): δ 13.206 (bs, 1H), δ 11.876 (s, 1H), δ 7.498-7.445 (m, 2H), δ 7.19 (d, J=2.0 Hz, 1.0H).

Workup

  1. additionmixed with a magnetic stirrer
  2. temperatureThis mixture was refluxed for 1 hour
  3. customThe THF was removed via rotary evaporator
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-360858ce3ccb424195bc5955489531fa
Source dataset
uspto-grants-2012_01
Patent number
US08088768B2

Linked notes

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