Methanesulfonyl chloride → HCID 22169652, compound

To a stirred solution of 2-fluoro-6-methylamino-benzonitrile (1.5 g, 10 mmol) in THF (50 mL) at −78° C. was added LiHMDS (1M in THF, 16 mL, 16 mmol) dropwise over 5 min. The resulting pale yellow solution was stirred for an additional 30 min, then methanesulfonyl chloride (1.16 mL, 15 mmol) was added. After 30 min, the reaction mixture was quenched with saturated NH4Cl (1 mL), diluted with ethyl acetate (100 mL), dried (MgSO4), filtered and concentrated to give viscous yellow oil. The crude product was purified on silica gel column (2:3 EtOAc/hexanes) to give the title compound as a white solid (1.5936 g, 70% yield). 1HNMR (500 MHz, CDCl3) δ: 7.65–7.61 (1H, m), 7.86 (1H, d, J=8.24 Hz), 7.22 (1H, t, J=8.24 Hz), 3.38 (3H, s), 3.13 (3H, s). HRMS (ESI) calcd for C17H22FN2O7S (M+H): 417.1132; found: 417.1116.

1. waitAfter 30 min
2. customthe reaction mixture was quenched with saturated NH4Cl (1 mL)
3. additiondiluted with ethyl acetate (100 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customto give viscous yellow oil
8. customThe crude product was purified on silica gel column (2:3 EtOAc/hexanes)

ORD record

ord-b594e1e91a8a405d8d411738a2170cf5

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037908B2