Methyl iodide → HCID 67996655, compound

Temperature

-78 °C

To the intermediate from Step A (1.35 g, 8.71 mmol) and HMPA (6.24 g, 34.8 mmol) in 10 mL of THF at −78° C. was added dropwise a LDA solution (2.0 M, 5.22 mL, 10.5 mmol). The mixture was stirred at −78° C. for 30 min and MeI (1.48 g, 10.45 mmol) was added dropwise. The resulting mixture was slowly warmed to room temperature. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase was washed with brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated compound (yellow oil). 1H NMR (CDCl3, 500 MHz) δ 7.48 (1H, s), 3.77 (3H, s), 3.76 (1H, q, J=7.5 Hz), 2.49 (3H, s), 1.55 (3H, d, J=7.5 Hz).

1. temperatureThe resulting mixture was slowly warmed to room temperature
2. customThe reaction was quenched with saturated aqueous NH4Cl solution
3. extractionextracted with EtOAc
4. washThe organic phase was washed with brine
5. dry with materialdried with MgSO4
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography
8. customto give the indicated compound (yellow oil)

ORD record

ord-bbe2b3a29c1e484a8532db76a3b36c3a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365574B2