3-(4-Amino-5-nitro-2'-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol → 3-(4,5-Diamino-2'-trifluoromethyl-biphenyl-3-yl)-propan-1-ol
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[CH:4][C:3]=1[C:21]#[C:22][CH2:23][OH:24]>[Pd].C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:19])[F:20])=[CH:4][C:3]=1[CH2:21][CH2:22][CH2:23][OH:24]Participants
Procedure
3-(4-Amino-5-nitro-2′-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol (148 mg, 0.440 mmol, as prepared in the previous step) was placed in an 8 mL vial equipped with a magnetic stir bar, and dry EtOH (2 mL) was added via syringe. To the ethanol solution was added 10% Pd on activated carbon (27 mg), and the vial was capped with a rubber septum. Hydrogen gas was bubbled through the stirred solution for 3 min, and the reaction was stirred under an atmosphere of H2 at 1 atm for 16 h. The vial was vented, the reaction was filtered, and the filter was washed three times with MeOH (5 mL). The solvent was removed under reduced pressure to give 101 mg (73%) of the desired compound. 1H-NMR (400 MHz, CDCl3) δ: 7.68 (d, J=7.6 Hz, 1H), 7.48 (t, J=7.3 Hz, 1H), 7.38 (t, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 6.61 (s, 1H), 6.60 (s, 1H), 3.65 (t, J=5.9 Hz, 2H), 3.48 (br. s., 4H), 2.66 (t, J=7.3 Hz, 2H), 1.86 (quin, J=6.6 Hz, 2H).
Workup
- customvial equipped with a magnetic stir bar
- customthe vial was capped with a rubber septum
- customHydrogen gas was bubbled through the stirred solution for 3 min
- filtrationthe reaction was filtered
- washthe filter was washed three times with MeOH (5 mL)
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-532b6d2556194d13b2b6f6a0769b8662
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232409B2
Reaction notes
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