Potassium Carbonate → HCID 22180716, compound

HRID 1795871Notes

Reaction equation

HRID 1795871 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([NH2:19])=[C:12]2[C:20]#[N:21])([O-])=O.C([O-])([O-])=O.[K+].[K+]>CO.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([NH2:19])=[C:12]2[C:20]#[N:21]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22180676HCID 22180676, compound

Product 1

HCID 22180716HCID 22180716, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(3-nitrobenzyloxy)-2-amino-1-methyl-1H-indole-3-carbonitrile (40 mg; 0.12 mol) in MeOH (6 ml) was treated with K2CO3 (6 mg) and hydrogenated over PtO2 (6 mg) at 45 psi at room temperature for 1 hour. After filtration and evaporation to dryness, the residue was purified by flash chromatography eluting with MeOH/CH2Cl2 (5% MeOH) and the appropriate factions were evaporated to give 5-(3-aminobenzyloxy)-2-amino-1-methyl-1H-indole-3-carbonitrile (32 mg).

Workup

  1. filtrationAfter filtration and evaporation to dryness
  2. customthe residue was purified by flash chromatography
  3. washeluting with MeOH/CH2Cl2 (5% MeOH)
  4. customthe appropriate factions were evaporated

Sources & evidence

ORD record
ord-89e88c5ae13749c3a31c3f6d125f8980
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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