2-Bromoanisole → HCID 89761777, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 1-bromo-2-methoxybenzene (0.056 ml, 0.454 mmol), N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.090 g, 0.303 mmol), Xantphos (0.035 g, 0.061 mmol), Pd2(dba)3 (0.028 g, 0.030 mmol) and sodium tert-butoxide (0.087 g, 0.908 mmol). The mixture was diluted with toluene (3.03 ml), and purged with nitrogen, and stirred at 130° C. in the microwave for 15 minutes, until clean conversion to the desired product. The reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo and further purified using a 2-g SCX column (product eluted with methanol wash). The crude material was concentrated and absorbed directly onto a 12-g RediSep Gold column and purified by silica-gel chromatography, eluting with a gradient of 0% to 100% ethyl acetate in heptanes to provide 4-(2-methoxyphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.59-3.65 (m, 2 H) 3.74 (s, 3 H) 4.29 (t, J=4.35 Hz, 2 H) 6.16 (d, J=8.41 Hz, 1 H) 6.76 (d, J=4.60 Hz, 1 H) 7.00-7.04 (m, 1 H) 7.04-7.11 (m, 2H) 7.17 (dd, J=8.31, 1.27 Hz, 1 H) 7.21 (d, J=4.60 Hz, 1 H) 7.28 (dd, J=7.78, 1.61 Hz, 1 H) 7.31-7.37 (m, 1 H) 12.52 (br. s., 1 H). m/z (ESI) 404.0 (M+H)+.

Provenance & Evidence