Trifluoroacetic acid → 2-(n-Butyl)-7-azaindole

HRID 248927Notes

Reaction equation

HRID 248927 reaction equation
C(OC([NH:8][C:9]1[C:14]([CH2:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:17]([C:16]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18946711HCID 18946711, compound

Product 1

HCID 177522782-(n-Butyl)-7-azaindoleYield 115.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[2-(t-butoxycarbonylamino)pyridin-3-yl]hexan-2-one (Y) (4.2 g) (prepared, e.g, as described in Preparation 18), in dichloromethane (25 ml) and trifluoroacetic acid (10 ml) was stirred at room temperature overnight. The solution was concentrated under vacuum and the residue was partitioned between aqueous ammonium hydroxide and ether. The ether layer was washed with brine, dried, and the solvent was evaporated. The residue was further purified by silica gel chromatography, eluting with 30% ethyl acetate-hexane, to give 2-(n-butyl)-7-azaindole (2.9 g), a compound of Formula (AB), as an oil, which crystallized on standing to a solid, m.p. 46°-47° C.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was partitioned between aqueous ammonium hydroxide and ether
  3. washThe ether layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated
  6. customThe residue was further purified by silica gel chromatography
  7. washeluting with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-aa9ff80eab0c438791a263f343d1b8f5
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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