Indole-2-carboxaldehyde → HCID 59772999, compound

HRID 2220697Notes

Reaction equation

HRID 2220697 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=O.[CH3:12][N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH2:18][CH2:19][NH2:20].[Na]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH:20][CH2:19][CH2:18][CH:14]1[CH2:15][CH2:16][CH2:17][N:13]1[CH3:12]

Participants

5

Reactant 3

HCID 96389Indole-2-carboxaldehydeHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 5360545Sodium

Product 1

HCID 59772999HCID 59772999, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 5, from 1H-indole-2-carbaldehyde 0.14 g (2 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethylamine 0.3 g (2.4 mmol), and sodium triacethoxyborohydride 0.87 g (1.87 mmol), in 20 mL Dichloromethane. The compound was purified using silica gel chromatography elution, ethyl-acetate-methanol-amonium hydroxide: 9-1-0.1 to 8-2-0.2, yield to 0.3 g light brown oil.

Workup

  1. customThe compound was purified
  2. washsilica gel chromatography elution, ethyl-acetate-methanol-amonium hydroxide

Sources & evidence

ORD record
ord-e085d2f7154b48178a4de9d6f65007e0
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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