HCID 10659117, compound → Ethyl 5-cyanoindole-2-carboxylate

HRID 1866231Notes

Reaction equation

HRID 1866231 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5](=O)[CH2:6][C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=1[N+:15]([O-])=O)[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:5]1[NH:15][C:8]2[C:7]([CH:6]=1)=[CH:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[O:19])[CH3:2]

Participants

5

Reactant 2

HCID 10659117HCID 10659117, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 4714953Ethyl 5-cyanoindole-2-carboxylateYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add to 1.2 g 3-(5-cyano-2-nitrophenyl)-2-oxopropionic acid ethyl ester 2 (m=0) in EtOH (40 mL), 10% Pd/C (0.40 g) and stir under a hydrogen atmosphere until the theoretical amount of hydrogen is absorbed. Filter the mixture and concentrate the filtrate to afford 1.1 g of crude product. Purify by chromatography on SiO2 eluting with CH2Cl2. Concentrate the desired fractions and vacuum dry the residue over night (40° C.) to provide the title compound (0.5 g) as white crystals, Rf=0.9 (silica gel, 10% MeOH/CH2Cl2).

Workup

  1. customis absorbed
  2. filtrationFilter the mixture
  3. concentrationconcentrate the filtrate
  4. customto afford 1.1 g of crude product
  5. customPurify by chromatography on SiO2 eluting with CH2Cl2
  6. concentrationConcentrate the desired fractions and vacuum
  7. customdry the residue over night (40° C.)

Sources & evidence

ORD record
ord-b68f38853a794debba4192ec02913f1e
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

Loading…