Trifluoroacetic acid → HCID 12085351, compound

HRID 1166189Notes

Reaction equation

HRID 1166189 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22997492HCID 22997492, compound

Product 1

HCID 12085351HCID 12085351, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (5-fluoro-1H-indole-3-yl)-pyridin-3-yl-methanol (5.00 g, 21 mmol) in methylene chloride is treated with triethylsilane (3.70 ml, 23 mmol) and trifluoroacetic acid (TFA), stirred at room temperature overnight, and concentrated in vacuo. The resultant residue is basified with 2.5 N NaOH and saturated NaHCO3, and extracted with methylene chloride. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. This residue is purified by column chromatography (50%EtOAc/CH2Cl2) to give the title compound as a pale orange solid 3.24 g (68%) mp 109-112° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with methylene chloride
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThis residue is purified by column chromatography (50%EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-253269dfebca491091d574af82b4755a
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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