5-Fluoro-6-isopropenyl-pyridin-2-ylamine → 5-Fluoro-6-isopropylpyridin-2-amine

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[N:6][C:7]=1[C:8]([CH3:10])=[CH2:9].[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[N:6][C:7]=1[CH:8]([CH3:9])[CH3:10]

Participants

Procedure

To a solution of 5-fluoro-6-isopropenyl-pyridin-2-ylamine (crude from last step, 4.45 mmol) in methanol (13.5 mL) was added 10% palladium on carbon (95 mg) at room temperature. A hydrogen balloon (1 atm) was attached and the mixture was stirred overnight. After 18 h, the mixture was filtered over Celite, concentrated on to silica gel, and chromatographed (10% to 40% EtOAc in hexanes) to give 5-fluoro-6-isopropylpyridin-2-amine (470 mg, 69% over two steps). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.12 (t, J=9.2 Hz, 1H), 6.30 (dd, J=8.5, 3.0 Hz, 1H), 4.31 (br. s, 2H), 4.15 (m, 1H), 1.26 (d, J=7.2 Hz, 6H).