(6-Bromo-5-fluoropyridin-2-yl)-tert-butylamine → 6-Bromo-5-fluoropyridin-2-amine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8]C(C)(C)C)[CH:5]=[CH:4][C:3]=1[F:13]>ClCCCl.C(O)(C(F)(F)F)=O>[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[F:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of (6-bromo-5-fluoropyridin-2-yl)-tert-butylamine (46 mg, 0.19 mmol) in DCE (2 mL) and TFA (2 mL) was heated at 120° C. for 10 min in a microwave reactor, and then concentrated under reduced pressure. The residue was taken up in MeOH and loaded onto an Isolute® SCX-2 cartridge (5 g). The cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH to give 6-Bromo-5-fluoropyridin-2-ylamine as an off-white solid (25 mg, 71%). 1H NMR (400 MHz, CHCl3-d): δ 7.21 (dd, J=8.7, 7.2 Hz, 1 H); 6.39 (dd, J=8.7, 2.7 Hz, 1 H); 4.89-3.75 (s, 2 H).
Workup
- concentrationconcentrated under reduced pressure
- washThe cartridge was washed with MeOH
- washthe desired product eluted with 2 M NH3 in MeOH
Sources & evidence
- ORD record
- ord-6ff17c1b88be409991979326ec296f80
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394796B2
Reaction notes
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