ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate → HCID 57108709, compound

HRID 2293295Notes

Reaction equation

HRID 2293295 reaction equation
[C:1]([O:5][C:6]([CH2:8]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:28]([C:30]1[C:38]2[C:33](=[CH:34][C:35]([Cl:40])=[CH:36][C:37]=2[Cl:39])[NH:32][C:31]=1[C:41]([O:43][CH2:44][CH3:45])=[O:42])=O>>[C:1]([O:5][C:6]([CH:8]=[CH:28][C:30]1[C:38]2[C:33](=[CH:34][C:35]([Cl:40])=[CH:36][C:37]=2[Cl:39])[NH:32][C:31]=1[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 2794948ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylateHCID 178451389HCID 178451389, compound

Product 1

HCID 57108709HCID 57108709, compoundYield 67.8%

Procedure

A solution of tertbutoxycarbonylmethyltriphenylphosphorane (5.33 g) and ethyl 3-formyl-4,6-dichloroindole-2-carboxylate (3 g) in dioxanlacetonitrile (1;1; 60 ml) was stirred at 60° for 7 hours. The solvent was evaported under reduced pressure and the residual oil was purified by chromatography, eluting with cyclohexane and ethyl acetate 7/3, to obtain the title compound (2,73 g) tlc EA/CH: 3/7; Rf=0.35.

Workup

  1. customthe residual oil was purified by chromatography
  2. washeluting with cyclohexane and ethyl acetate 7/3

Sources & evidence

ORD record
ord-11ba3d8ff926486d91e4e4e9821afd67
Source dataset
uspto-grants-1997_11
Patent number
US05686461

Reaction notes

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