Dimethylformamide → HCID 44545776, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(text-butoxycarbonyl-methyl-amino)-benzoic acid (70 mg, 0.28 mmol) in CH2Cl2 (2 mL) was added 1-chloro-N,N-2-trimethylpropenylamine (98 μL, 0.74 mmol). Following formation of the resulting acid chloride, the reaction mixture was concentrated affording a residue that was dissolved in pyridine (2 mL) before 2,6-difluoro-pyridin-3-ylamine (30 mg, 0.23 mmol) was added in one portion. After an additional 30 minutes the reaction mixture was concentrated to dryness affording a residue to which was added DMF (2 mL) and K2CO3 (64 mg, 0.46 mmol). The resulting mixture was heated by microwave to 150° C. for 10 min, after which the resulting mixture was filtered, concentrated and purified by silica gel flash chromatography (0 to 100% EtOAc in hexanes) to afford [4-(5-fluoro-oxazolo[5,4-b]pyridine-2-yl)-phenyl]-methyl-amine (50 mg, 0.21 mmol, 89%). ES MS (M+H+)=244; 1H NMR (300 MHz, DMSO-d6): δ 8.24 (t, J=7.7 Hz, 1H); 7.89 (d, J=8.4 Hz, 2H); 7.18 (d, J=8.4 Hz, 1H); 6.68 (d, J=8.5 Hz, 3H); 2.76 (s, 3H); HRMS m/z 244.0883 (C13H10FN3O+H+ requires 244.0881).

Provenance & Evidence