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

HRID 2374008Notes

Reaction equation

HRID 2374008 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) 68.65 (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-95ba9f53d32a4e788b46b51e7eb3ccd2
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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