Sodium Hydroxide → 1h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-n-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-

HRID 855413Notes

Reaction equation

HRID 855413 reaction equation
[C:1]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[OH-].[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH2:19][CH2:18]3)=[O:12])=[CH:31][CH:32]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 866030491H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

Product 1

HCID 768468731h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-n-[2-(4-fluorophenyl)ethyl]-2,3-dihydro-Yield 47.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 95 mg (0.22 mmol) of 1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide in 2 ml conc. acetic acid 46 mg of sodium borohydride (0.67 mmol) were added in three portions (ice bath cooling). The reaction mixture was stirred for 3 h at rt, then treated with 2N NaOH to adjust the pH to 12, extracted twice with diethylether and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:4) to give 45 mg white foam (45%). MS(ISP) 431.5 (M+H)+.

Workup

  1. extractionextracted twice with diethylether
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-abc651f34a754640acb125e6f964ca9e
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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