Dimethylformamide → HCID 178480269, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of isopropylmagnesium bromide (3 mL, 2.97 mmol, 1.0 M solution in THF) was added n-butyllithium (2.4 ml, 5.93 mmol, 2.5 M solution in hexane). The mixture was cooled to −78° C., and then a solution of Example 9G (0.680 g, 1.48 mmol) in THF (2 mL) was added dropwise. The mixture was stirred for 1 hour at −78° C. then DMF (0.460 mL, 5.93 mmol) was added, and the mixture was allowed to warm to room temperature. The mixture was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine and concentrated under reduced pressure. Purification of the residue by chromatography (silica gel, eluted with a gradient of 5-50% hexanes in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) afforded the title compound (560 mg, 1.374 mmol, 93% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.52 (m, 4H), 1.24-1.36 (m, 1H), 1.42 (s, 9H), 3.98 (s, 3H), 4.30 (d, J=7.14 Hz, 2H), 6.92 (s, 1H), 7.33-7.43 (m, 1H), 7.70-7.78 (m, 1H), 8.7 (dd, J=6.74, 2.38 Hz, 1H), 10.58 (s, 1 H); MS (ESI) m/z 408 [M+H]+, 406[M−H]−.

Provenance & Evidence