Acetic Acid → Furo[2,3-c]pyridin-7-amine

N-methoxyfuro[2,3-c]pyridin-7-amine (43.0 g, 0.26 mol) in DCM (200 mL) was cooled in a water bath. Zinc dust (36.0 g, 0.64 mol) was added in one portion and stirred for a few min. Acetic acid (18.8 g, 0.31 mol) was added slowly over 5-10 min and stirred for 30 min. The water bath was removed and the mixture was stirred at RT for 16 h. At this point, TLC analysis (5% MeOH in DCM) indicated complete consumption of the starting material. The mixture was diluted with 400 mL of DCM and washed with saturated NaHCO3 until the pH of the wash was about 8.5. The DCM layer was then washed with water (2×100 mL) and then brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by flash chromatography (2% MeOH:DCM) to provide 34 g (97%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 4.89 (br s, 2H), 6.71 (d, J=1.8 Hz, 1H), 6.94 (d, J=5.4 Hz, 1H), 7.63 (d, J=1.8 Hz, 1H), 7.84 (d, J=5.4 Hz, 1H).

1. stirringstirred for 30 min
2. customThe water bath was removed
3. stirringthe mixture was stirred at RT for 16 h
4. customconsumption of the starting material
5. additionThe mixture was diluted with 400 mL of DCM
6. washwashed with saturated NaHCO3 until the pH of the wash
7. washThe DCM layer was then washed with water (2×100 mL)
8. dry with materialThe solution was dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe resulting crude product was purified by flash chromatography (2% MeOH:DCM)

ORD record

ord-08ec2c4962f142e7a1ab2d952889bef6

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2