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

HRID 1769209Notes

Reaction equation

HRID 1769209 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 189467111-[2-(t-Butoxycarbonylamino)pyridin-3-yl]hexan-2-one

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 (42) (4.2 g) (prepared, e.g, as described in Preparation 29), 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 (43), 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-4ad807714af1408d8b525e7bfd59c640
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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