Ethylene Glycol → HCID 22504363, compound

HRID 1432245Notes

Reaction equation

HRID 1432245 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=2)=[CH:4][CH:3]=1.O.NN.[OH-].[K+].C(O)CO>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22504441HCID 22504441, compound

Product 1

HCID 22504363HCID 22504363, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

1-(4-fluorobenzyl)-5-methanesulfonyl-2-nicotinoylindole (0.14 g), hydrazine monohydrate (0.17 g), potassium hydroxide (0.05 g) and ethylene glycol (3 ml) were added under nitrogen atmosphere and the mixture was stirred at 110° C. for 8 hours. To the reaction solution was added water; and the mixture was extracted with dichloromethane, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was subjected to siilica gel column chromatography (hexane:ethyl acetate=1:3) to obtain 13 mg of the desired product.

Workup

  1. extractionand the mixture was extracted with dichloromethane
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69bc1ffdfbff43a5b62b399dc5f05693
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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