Trifluoroacetic acid → 2-Propyn-1-amine, 3-[4-(2-fluoro-4-nitrophenoxy)-3-pyridinyl]-

HRID 1670261Notes

Reaction equation

HRID 1670261 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][CH2:13][NH:14]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59852906HCID 59852906, compound

Product 1

HCID 598529072-Propyn-1-amine, 3-[4-(2-fluoro-4-nitrophenoxy)-3-pyridinyl]-Yield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)prop-2-ynylcarbamate (300 mg, 0.78 mmol) in CH2Cl2 (10 mL) was treated with TFA (2 mL) and stirred at rt for 45 min. The mixture was concentrated under vacuum and the residue was partitioned between EtOAc and saturated aq. NaHCO3 solution. The EtOAc phase was separated and washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (180 mg, 80%) as a red oil. 1H NMR (DMSO-d6) δ 8.65 (s, 1H), 8.47 (d, 1H, J=5.6 Hz), 8.43 (dd, 1H, J=10.7, 2.5 Hz), 8.17 (d, 1H, J=8.6 Hz), 7.54 (t, 1H, J=8.6 Hz), 7.04 (d, 1H, J=5.6 Hz), 3.49 (s, 2H); MS (ESI+): m/z 288.17 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was partitioned between EtOAc and saturated aq. NaHCO3 solution
  3. customThe EtOAc phase was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-986e734dfa7148abb0f113df1d3b0d84
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

Loading…