Tetrahydrofuran → HCID 18385416, compound

HRID 1250208Notes

Reaction equation

HRID 1250208 reaction equation
N(C([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=1)=O)=[N+]=[N-].C1[CH2:24][O:23]CC1.[Br-].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35](=[O:38])[CH2:36][NH3+:37])=[CH:27]1.C([N:41](C(C)C)C(C)C)C>C1C=CC=CC=1>[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([C:35](=[O:38])[CH2:36][NH:37][C:24](=[O:23])[NH:41][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=2)=[CH:27]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 12243795HCID 12243795, compoundHCID 18385438HCID 18385438, compound

Product 1

HCID 18385416HCID 18385416, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-(azidocarbonyl)-1-(ethoxycarbonyl)indole Suvorov (ibid) (1.32 g, 5.12 mmol) in benzene (25 ml) was heated to reflux for 7 hours. After cooling to room temperature, THF (25 ml) and [2-(3-indolyl)-2-oxoethyl]ammonium bromide [Oikawa,Y. et al. Heterocycles 12 (1979) 1457-1462] (1.31 g, 5.12 mmol) were added immediately followed by ethyldiisopropylamine (0.89 ml, 5.12 mmol). After stirring for 1.5 hours the formed precipitate was removed by filtration and washed with THF followed by water. The sub-title compound (1.65 g, 79%) was obtained as a white solid after drying.

Workup

  1. temperatureto reflux for 7 hours
  2. customwas removed by filtration
  3. washwashed with THF

Sources & evidence

ORD record
ord-405bfea965ab42ef86eb784655028e4e
Source dataset
uspto-grants-2002_01
Patent number
US06337342B1

Reaction notes

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