HCID 46898224, compound → HCID 46898225, compound

HRID 602798Notes

Reaction equation

HRID 602798 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH:12]([C:14]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[CH:32])[CH:26]=4)(=[O:24])=[O:23])([F:21])[C:15]4[O:16][C:17]([CH3:20])=[N:18][N:19]=4)[CH2:13][C:5]=3[C:4]=2[CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH:12]([C:14]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH3:32])[CH:26]=4)(=[O:23])=[O:24])([F:21])[C:15]4[O:16][C:17]([CH3:20])=[N:18][N:19]=4)[CH2:13][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 46898224HCID 46898224, compound

Product 1

HCID 46898225HCID 46898225, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 22 mg (0.05 mmol) (RS, SR)-7-chloro-2-[(3-ethynyl-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-1,2,3,4-tetrahydro-cyclopenta[b]indole in 0.5 mL of methanol was treated with 1 mg of palladium on activated charcoal (10%) and stirred intensely under H2 (atmospheric pressure) during 5 hrs. Filtration and evaporation of the solvent gave 21 mg (92%) of (RS, SR) 7-chloro-2-[(3-ethyl-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-1,2,3,4-tetrahydro-cyclopenta[b]indole, as a yellow solid, MS: 475 (MH+)

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-629769dd684543b7854b53234fd9ff60
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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