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A mixture of 5-bromonicotirsaSdehydbeta (1.860 g, 10 mrnof), ethanes utfonamtde (1.091 g, 10.00 mmo.) and titanium(iV) isopropoxide (5.86 mi, 20.00 mmoi) in Toluene (20 mL) was heated to reflux for 2 hr. After concentration, the residue was dissolved in THF (25 mL) and cooled to -40 0C. A solution of cyclopropyimagnesiurn bromide (50-0 ml, 25.00 mmoi) was added dropwise and the resuiting mixture was slowly warmed up to -20 0C and stirred at this temperature for 4 hr. After quenched by NH4C1 soiution, filtration, extraction with CH2C12, the solution was dried over Na2SO4, and concentrated, the residue was purified by flash column (ethyi acetate / heptane, v/v, 10percent-35percent) and yielded the title compound (1.5 g). 1H MMR (400.3 MHz, CDCf3); delta 0.2-0.3 (m, 1H)1 0.4-0.5 (m, IH)1 0.5-0.6 (m, 1H)1 0.6-0.7 (m, 1H), 1.0-1.1 (m, 1H)1 1.1-12 (m, 3H), 2.55-2.75 (m. 2H)1 3,6-3.7 <;m, 1 H), 4.51 (brd, J ~ 4.8 Hz, 1H)1 7.73 (s, 1H)r 8.42 (S, 1 H), 8.51 (S1 1H). |
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A mixture of 5-bromonicotinaldehyde (372 mg, 2 mmo.),<strong>[1520-70-3]ethanesulfonamide</strong> (273 mg, 2.500 mmol) and tttanium(IV) isopropoxide (1172 mul, 4.00 mmol) m toluene (20 mL) was heated to reflux for 2 h. After concentration, the residue was dissolved in THF (25 mL) and cooled to -400C. A solution of cyclopropyimagnesium bromide (10 mL, 5.00 mmol) was added dropwise and the resulting mixture was slowly warmed up to -200C and stirred at this temperature for 4 h. After quenching by saturated NH4CI solution, filtration, extraction with CH2CI7, the solution was dried over Na2SO4, and concentrated. The residue was purified by flash column (ethyl acetate / heptane, v/v, 10percent-35percent) and yielded the title product as oil (430 mg). 1H NMR (400 MHz, CDCI3): 80.2-0.3 (m, 1H)1 0.4-0.5 (m, 1H)1 0.5-0.6 (m. 1H), 0.6-0.7 (m, 1H), 1.0-1.1 (m, 1H), 1.1-1.2 (m, 3H). 2.55-2.75 (m,2H). 3.6-3.7 <;m, 1H)1 4.51 (brd. J = 4.8 Hz, 1H). 7.73 <;s, 1H). 8.42 (s, 1H), 8.51 (s, 1H). |
| 0.59 g |
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Step A: To a mixture of 5-bromonicotinaldehyde (0.50 g, 2.69 mmol) and <strong>[1520-70-3]ethanesulfonamide</strong> (0.37 g, 3.36 mmol) in 9.0 mL of toluene is added titanium(IV) isopropoxide (1.59 mL, 5.4mmol). The reaction mixture is stined at 120°C for 3 hours after which time it is concentrated to dryness. The remaining residue is dissolved in 10 mL of THF and cooled to -40°C. Cyclopropylmagnesium bromide (16.13 mL, 8.1 mmol) is added drop-wise and the reaction mixture is allowed to gradually warm to room temperature. After 16 hours, the reaction mixture is diluted with EtOAc and washed with saturated aqueous NH4C1 solution then brine. The organic layer is dried (Mg504), filtered and concentrated. The remaining residue is purified via silica gel flash column chromatography eluting with 0-5percent MeOH/DCM to give 0.59 g of ethanesulfonic acid [(5-bromo-pyridin-3-yl)-cyclopropyl-methyl] -amide. |
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