Pyridine → HCID 19418854, compound

HRID 2395761Notes

Reaction equation

HRID 2395761 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.N1C=CC=CC=1.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:22]([O:29][C:30]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylate

Product 1

HCID 19418854HCID 19418854, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 5-aminoindole-2-carboxylate [J. Am. Chem. Soc. 80, 4621 (1958) JCS Perkin I 53 (1977), 0.50 g] is dissolved in 49 ml of methylene chloride and pyridine (0.20 g) is added. The reaction is cooled to 0° and benzylchloroformate (0.36 ml) is added dropwise over 10 min. The reaction is stirred for 1 hr, diluted with chloroform, washed with saturated aqueous sodium bicarbonate, water, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate is purified by flash column chromatography (150 g silica gel) eluting with hexane/ethyl acetate (3/1). The appropriate fractions are pooled and concentrated to give the title compound, NMR (300 MHz, CDCl3) 8.90, 7.79, 7.41-7.33, 7.24, 7.16, 5.22, 4.40 and 1.41 δ.

Workup

  1. temperatureThe reaction is cooled to 0°
  2. washwashed with saturated aqueous sodium bicarbonate, water, saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by flash column chromatography (150 g silica gel)
  6. washeluting with hexane/ethyl acetate (3/1)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6ea1227aeef4aeea12645fdf204228f
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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