N-but-2-enyl-2,2,2-trifluoro-N-(5-fluoro-3-iodo-pyridin-2-yl)-acetamide → HCID 68556425, compound

Temperature

100 °C

A solution of N-but-2-enyl-2,2,2-trifluoro-N-(5-fluoro-3-iodo-pyridin-2-yl)-acetamide (2.57 g, 6.5 mmol) in DMF (10 mL) is treated with n-Bu4NCl (2 g, 7.15 mmol), Pd(OAc)2 (59 mg, 0.26 mmol), and stirred at 100° C. for 2 h. The mixture is cooled to rt, diluted with EtOAc (50 mL), filtered through a pad of silica gel, and washed with 1 M HCl (50 mL). The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 25%-70% EtOAc in heptane to afford 3-ethyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (0.75 g, 70%). MS: 165 (M+H); 1H NMR (300 MHz, CDCl3): δ 9.62 (s, NH, 1H), 8.17 (m, 1H), 7.60 (m, 1H), 7.16 (s, 1H), 2.74 (q, 2H), 1.31 (t, 3H).

1. temperatureThe mixture is cooled to rt
2. filtrationfiltered through a pad of silica gel
3. washwashed with 1 M HCl (50 mL)
4. customThe organic layer is separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue is purified by silica gel chromatography
9. washeluting with 25%-70% EtOAc in heptane

ORD record

ord-f146c707cab1449d830bd66afc623492

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258130B2