Lithium Hydroxide → HCID 57887234, compound

HRID 1819689Notes

Reaction equation

HRID 1819689 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:12])=[C:5]2[CH2:13][C:14]([O:16]C)=[O:15].[Li+].[OH-:19].[CH3:20]COC(C)=O.[CH2:26]1[CH2:30]OC[CH2:27]1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:19])[NH:12][C:26]([CH3:27])([CH3:30])[CH3:20])=[C:5]2[CH2:13][C:14]([OH:16])=[O:15].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:12])=[C:5]2[CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 69056328HCID 69056328, compound

Product 2

HCID 57887234HCID 57887234, compoundYield 94.7%HCID 57887237HCID 57887237, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step J (2): To a solution of methyl 2-(5-bromo-2-cyano-1H-indol-3-yl)acetate (50 mg, 0.17 mmol) in THF (1.0 mL) was added a solution of LiOH (12 mg, 0.5 mmol) in water (0.5 mL). The mixture was stirred at rt for 3 h. 100 mL of EtOAc was added, and the resulting solution was washed with 0.1 N HCl and water. The organic layer was dried over Na2SO4, and the solvents was removed to give 45 mg of the title compound 2-(5-bromo-2-cyano-1H-indol-3-yl)acetic acid (yield 94.7%) which was used without further purification. 1H NMR (500 MHz, CDCl3) δ ppm 3.89 (s, 2 H) 7.34 (d, J=8.85 Hz, 1 H) 7.43 (dd, J=8.85, 1.83 Hz, 1 H) 7.83 (d, J=1.53 Hz, 1 H).

Workup

  1. washthe resulting solution was washed with 0.1 N HCl and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvents was removed

Sources & evidence

ORD record
ord-62b6e04c190b42cfae599ca8b3678a74
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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