2-(5,6-dihydro-2H-4-pyranyl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole → HCID 22504413, compound

HRID 1432256Notes

Reaction equation

HRID 1432256 reaction equation
[O:1]1[CH2:6][CH2:5][C:4]([C:7]2[N:8]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=3)=[CH:3][CH2:2]1>[C].[Pd].C(O)C>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:8]2[C:9]3[C:14](=[CH:13][C:12]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:11][CH:10]=3)[CH:15]=[C:7]2[CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 98215002-(5,6-dihydro-2H-4-pyranyl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole

Product 1

HCID 22504413HCID 22504413, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 2-(5,6-dihydro-2H-4-pyranyl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole (83 mg), 10% palladium carbon (15 mg) and ethanol (5 ml) was stirred at 15 to 30° C. for 24 hours under hydrogen atmosphere. The mixture was filtered and the mother liquid was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=0.2:1) to obtain 40 mg of the desired product as a white crystal.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe mother liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9dbebac8df65445d84c45cf0269f48af
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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