Sodium Hydroxide → HCID 57800231, compound

HRID 2101928Notes

Reaction equation

HRID 2101928 reaction equation
C([N:4]1[C:12]2[C:7](=[C:8]([C:14]([F:17])([F:16])[F:15])[C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:18])(=O)C.[OH-].[Na+]>CO.O>[Br:13][C:9]1[C:8]([C:14]([F:16])([F:15])[F:17])=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH:5]([CH3:18])[CH2:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578002541-Acetyl-5-bromo-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole

Product 1

HCID 57800231HCID 57800231, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 1-acetyl-5-bromo-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole (0.130 g, 0.404 mmol; step B above) and NaOH (0.086 g; 2.15 mmol) in MeOH/H2O (4:1; 13 mL) was heated at reflux 3 h. The solvent was removed, the residue was partitioned between Et2O/H2O, and the layers were separated. The aqueous layer was extracted with Et2O (×2). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo, affording 0.090 g of the title compound as a pale yellow oil which was used without further purification: MS (APCl) m/z 282 (M+H, 81Br).

Workup

  1. temperaturewas heated
  2. temperatureat reflux 3 h
  3. customThe solvent was removed
  4. customthe residue was partitioned between Et2O/H2O
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with Et2O (×2)
  7. washCombined organics were washed (H2O, brine)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68b8ea030c9d46b897cf5b475ab296e4
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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