Hydrochloric Acid → HCID 12068608, compound

HRID 1824975Notes

Reaction equation

HRID 1824975 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]([O:17]CC)=[O:16])=[CH:9]2)([O-:5])=[O:4].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH2:23]Cl.Cl>CS(C)=O.O>[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:22]=1[CH2:23][N:11]1[C:12]2[C:8](=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:14][CH:13]=2)[CH:9]=[C:10]1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 5815702,6-Difluorobenzyl chloride

Product 1

HCID 12068608HCID 12068608, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Under an atmosphere of argon, 5.49 g (83.2 mmol, 85% pure) of potassium hydroxide (powder) are initially charged in 110 ml of dimethyl sulphoxide, 6.43 g (27.5 mmol) of ethyl 5-nitro-1H-indole-2-carboxylate (A. Guy, J.-P. Guetté, Synthesis 1980, 222–223) are added at RT and the mixture is stirred for 30 min. With ice-cooling, at an internal temperature of 5–10° C., 2,6-difluorobenzyl chloride (10.0 g, 61.5 mmol) is then added dropwise over a period of 15 min, and the mixture is stirred at RT for 16 h. For work-up, the mixture is poured into 500 ml of water and acidified with dil. hydrochloric acid and the precipitated solid is filtered off with suction and pre-purified chromatographically on silica gel 60 (mobile phase gradient dichloromethane→dichloromethane-methanol 3:1). The resulting product is recrystallized from ethanol. This gives 4.33 g (47% of theory) of a pale-yellow crystalline solid.

Workup

  1. customGuetté, Synthesis 1980, 222–223)
  2. additionare added at RT
  3. additionis then added dropwise over a period of 15 min
  4. stirringthe mixture is stirred at RT for 16 h
  5. filtrationthe precipitated solid is filtered off with suction
  6. custompre-purified chromatographically on silica gel 60 (mobile phase gradient dichloromethane→dichloromethane-methanol 3:1)
  7. customThe resulting product is recrystallized from ethanol

Sources & evidence

ORD record
ord-f79b868f43c74c868b38b87eb6e6ad07
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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