Related Products of 139022-25-6 , The common heterocyclic compound, 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, its 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.
[0227] Step 5A. (R)-N- [[4-(3 ,5-difluorophenyl)sulfinylphenyll methyll imidazo [1,2- alpyridine-6-carboxamide. A solution of imidazo[1,2-a]pyridine-6-carboxylic acid (100 mg, 0.62 mmol, 1.50 equiv), EDCI (94.7 mg, 0.49 mmol, 1.20 equiv), HOBt (67 mg, 0.50 mmol,1.20 equiv), and diisopropylethylamine (160 mg, 1.24 mmol, 3.00 equiv) in DMF (10 mL) was stirred at 25 C for 30 mi [4-[(R)-(3,5-Difluorobenzene)sulfinyl]phenyl]methanamine (110 mg, 0.41 mmol, 1.00 equiv) was then added and the resulting solution was stirred for 12 h at 25 C. The reaction mixture was quenched with 50 mL of water. The resulting mixture was extracted with 2×50 mL of dichloromethane. The combined organic layers were washed with lxi 00 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (100/5) to give 35 mg (2 1%) of the title compound as a white solid. Chiral HPLC, Column: CHIRALPAK AD-H, Column size: 0.46*25 cm, 5 um, Mobile phase: Hexane/EtOH = 50/50 (0.1% TEA), Flow: 1.0 mL/min, Pressure: 5.0 MPa, Detector: UV-254 nm, Temperature: 25C, RT = 11.4 mi LC/MS (Method B, ESI): RT = 1.98 mi m/z = 412.1 [M+Hf?. ?H NMR (400 MHz, CD3OD) oe 9.04 (s, 1H), 7.96 (s, 1H),7.75 (d, J = 8.4 Hz, 2H), 7.71 (s, 1H), 7.66 (s, 1H), 7.59 (m, 3H), 7.35 (d, J = 4.8 Hz, 2H),7.10 (m, 1H), 4.66 (s, 2H). ?9F NMR (400 MHz, CD3OD) oe: -108.1.
The synthetic route of 139022-25-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; GOSSELIN, Francis; ZAK, Mark; ZHENG, Xiaozhang; WO2013/130935; (2013); A1;,
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