Trifluoroacetic acid → HCID 21268184, compound

HRID 1901012Notes

Reaction equation

HRID 1901012 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21268269HCID 21268269, compound

Product 1

HCID 21268184HCID 21268184, compound

Procedure

6-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (2.4 g, 9.9 mmol) was stirred in trifluoroacetic acid (10 mL) at room temperature under an atmosphere of nitrogen. Triethylsilane (1.65 mL, 10.4 mmol) was slowly added. After an initial exotherm, the mixture was stirred at room temperature for 12 hours. The mixture was concentrated under reduced pressure to yield a dark residue. The crude product was crystallized from ethanol to yield the title compound as a yellow crystalline solid. Yield 2.4 g (67%). mp 215°-217° C. FDMS m/e=245 (M+ of free base).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto yield a dark residue
  3. customThe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-d036d91b82484d12b7daabfef8475bb4
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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