Tetrahydrofuran → HCID 18385416, compound

HRID 2298030Notes

Reaction equation

HRID 2298030 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 prepared according to 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. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. customwas removed by filtration
  4. washwashed with THF

Sources & evidence

ORD record
ord-702c402fe3ac40a8a8f17f801d533fa0
Source dataset
uspto-grants-2002_12
Patent number
US06492409B1

Reaction notes

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