Sodium Hydroxide → HCID 86659886, compound

HRID 2360165Notes

Reaction equation

HRID 2360165 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[C:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:19])[CH:9]=1)=[O:6])[CH2:2][CH3:3].C([BH3-])#N.[Na+].[OH-].[Na+]>FC(F)(F)C(O)=O.C(OCC)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:19])[CH2:9]1)=[O:6])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86659885HCID 86659885, compound

Product 1

HCID 86659886HCID 86659886, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3-(di-n-propylaminocarbonylmethyl)-5-methoxy-1-methylindole (78.5 mg, 0.310 mmol) in 0.75 mL of trifluoroacetic acid was added sodium cyanoborohydride (79 mg, 1.3 mmol) at room temperature. After the reaction mixture was stirred at the same temperature for 12 h, the reaction mixture was diluted with diethyl ether, and neutralized by 40% sodium hydroxide aqueous solution. The separated organic layer was washed with saturated NaHCO3 aqueous solution and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (63 mg, 83%).

Workup

  1. washThe separated organic layer was washed with saturated NaHCO3 aqueous solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b571a2d4d5f4d719cce5eac32a5dae2
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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