HCID 22505858, compound → HCID 58947886, compound

HRID 2357106Notes

Reaction equation

HRID 2357106 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[N:11]([CH:21]2[CH2:25][CH:24]([OH:26])[CH:23]([CH2:27][OH:28])[O:22]2)[CH:10]=1)=[O:4].[H][H].C1(C)C=CC=CC=1.C(OC(=O)C)C.CO>[Pd].C(O)C>[NH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:21]1[CH2:25][CH:24]([OH:26])[CH:23]([CH2:27][OH:28])[O:22]1)[CH:10]=[C:9]2[CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:30])([F:29])[F:1]

Participants

6

Reactant 3

HCID 22505858HCID 22505858, compoundHCID 23144002HCID 23144002, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58947886HCID 58947886, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4.0 g (9.3 mmol) 2,2,2-Trifluoro-N-{3-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-nitro-1H-indol-3-yl]-prop-2-ynyl}-acetamide and 650 mg 5% (w/w) palladium on charcoal (Fluka No: 75992) were suspended in 100 ml anhydrous ethanol and placed under argon atmosphere in a flask. The argon was substituted by hydrogen (Whatman hydrogen generator). The hydrogenation was monitored by TLC (Silica Gel Merck F60, developing solvent: toluene/acetic acid ethyl ester/methanol 4:1:1 (v/v/v)) and stopped when the starting material was no longer detectable. The catalyst was removed by filtration and the solvent evaporated to dryness in a vacuum on a rotary evaporator. The product was used without further purification (yield: 3.7 g).

Workup

  1. customplaced under argon atmosphere in a flask
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated to dryness in a vacuum on a rotary evaporator
  4. customThe product was used without further purification (yield: 3.7 g)

Sources & evidence

ORD record
ord-058e8dced6a544f4ad6645ee091db626
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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