Some common heterocyclic compound, 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, molecular formula is C7H9IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine
A mixture of compound S4 (90.0 mg, 286 lirnol, I equiv), and iodo-diazirine S7 (70.0 mg, 286 imol, 1.00 equiv) was dissolved in DMF (3.0 rnL) at 24 C. To this mixture, was added potassium carbonate (40.0 mg, 286 umol, 100 equiv) and stirred for 12 hours at 24 C. The reaction mixture was partitioned between ethyl acetate (30 mL) and DI water (15 mL) and the organic portion was separated and washed with brine (3 x 15 mL). The combined organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford an off white powder. The powder was purified by flash column chromatography (30—60% ethyl acetate–hexane, three steps) to afford photo-celecoxib (5) as a white powder (92.0 nig, 75Rf = 0.20 (40% ethyl acetate—hexane; UV). ?H NMR (500 MHz, CDCI3): oe 8.05 (d, 21-1, J 8.2 Hz, H3). 8.02 (d, 2H, J 8.1 Hz, Fl4), 5.95 (s, iH, H?), 5.13 (br, 2H, H5), 4.04 (t,21-1, J 7.2 Hz, H2). 2.05—2.03 (in, 51-1, E-16/I-18/H9), i.71—i.69 (in, 21-1. H7). ?3C N]?[R (125 MIz, CDCI3): d 154.6 (C), 143.0 (q, 2JCF = 38.8 Hz, CH), 141.1 (C), 140.4 (C), 127.6 (CH), 122.5 ((1-1), 121.7 (q, IJCF 267.5 Hz CF3), 5.3 (C), 82.4 (C), 69.7 (CH). 67.6 (OCH2),32.4 (CH2), 32.1 (CH2), 26.1 (CN2), 13.2 (CH3). ?9FvR(375 MHz, CDCI3): -63.6. IR (ATR-FT1R), cnf?: 3277 (br), 1590 (s), 1563 (m), 1512 (m), 1490 (w), 1416 (m), 1380 (w), 1335 (w), 1246 (m), 1151 (rn), 1101 (rn), 968 (w), 908 (w), 40 (w), 743 (w), 715 (w), 626 (in), 543 (w). HRMS-ES1 (m/z): [M+F1] calculated for Ci7H,7F3NsO3S, 428,0999; found,428.0949.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1450754-38-7, its application will become more common.
Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WOO, Christina, M.; GAO, Jinxu; (555 pag.)WO2018/226828; (2018); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com