Lithium Hydroxide → HCID 67036415, compound

HRID 1623479Notes

Reaction equation

HRID 1623479 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH3:21])[C:12]2=[O:29])[CH:5]=1.[OH-].[Li+]>C1COCC1.O>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:20](=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[C:12]2=[O:29])[CH3:21])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67036322HCID 67036322, compound

Product 1

HCID 67036415HCID 67036415, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.33 g, 0.82 mmol) was dissolved in THF 5 ml. Then a solution of lithium hydroxide (0.35 g, 8.2 mmol) in water (2.0 ml) was added. After stirring for 12 hours, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid as yellow powder (100 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (s, 3H) 5.06 (s, 2H) 6.08 (d, J=7.83 Hz, 1H) 6.68 (t, J=7.45 Hz, 1H) 6.92 (d, J=7.83 Hz, 1H) 7.11 (t, J=7.45 Hz, 1H) 7.38 (t, J=8.84 Hz, 2H) 7.43-7.51 (m, 1H) 7.46 (dd, J=8.72, 5.68 Hz, 2H) 7.60 (d, J=7.58 Hz, 1H) 7.85 (d, J=7.83 Hz, 1H) 7.92 (s, 1H) 13.03 (s, 1H). MS calcd. for C24H18FNO3 387.4, obsd. (ESI+) [(M+H)+] 388.2.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 ml DMF
  3. customfor prepared HPLC

Sources & evidence

ORD record
ord-0d39b84786324e2a85dcec9ecf80b75c
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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