Methyl iodide → HCID 10537009, compound

Temperature

0 °C

To a suspension of NaH (2.63 g 6.6 mmol) in 200 mL of N,N-dimethylformamide at 0° C. was added a solution of (tert-butoxy)-N-[6-methyl-(2-pyridyl)]carboxamide (12.3 g, crude), as prepared in the preceding step, in 50 mL of N,N-dimethylformamide. The reaction stirred at 0° C. for 15 min then at ambient temperature for 1 h. Then iodomethane (10.22 g, 7.2 mmol) was added and the mixture was stirred at ambient temperature overnight (16 h). The reaction mixture was concentrated in vacuo, diluted with saturated NH4Cl (400 mL), and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel (10% ethyl acetate in hexane) to give the title compound as a yellow oil (7.56 g, 57%). 1H-NMR (400 MHz, DMSO-d6) δ 7.63 (t, J=7.2 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 6.97 (d, J=6.9 Hz, 1H), 3.27 (s, 2H), 2.42 (s, 3H), 1.45 (s, 9H).

1. waitat ambient temperature for 1 h
2. stirringthe mixture was stirred at ambient temperature overnight (16 h)
3. concentrationThe reaction mixture was concentrated in vacuo
4. additiondiluted with saturated NH4Cl (400 mL)
5. extractionextracted with ethyl acetate (2×250 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by flash chromatography on silica gel (10% ethyl acetate in hexane)

ORD record

ord-86a0f739ad4f4f8587fe79604f2044a5

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241789B2