Electric Literature of 637031-88-0 , The common heterocyclic compound, 637031-88-0, name is 3,3-Difluorocyclobutanol, molecular formula is C4H6F2O, 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.
A slurry of Intermediate 100 (40 mg, 0.085 mmol), 3,3-difluorocyclobutanol (11.5 mg,106 rnmoi), (4,4-di-t-butyi-2,2-bipyridine)bis[3,5-difluoro-2-[5-trifluoromethyi-2-pyridinyi- kappaN)phenyl-kappaCjiridium(lli) hexatluorophosphate (087 mg, 0.85 Itmol), nickei(ll) bromide ethylene glycol dimethyl ether complex (1.3 mg, 4.3 jimol), 4,4-di-tert-butyl-2,2- hipyridine (1.1 mg, 4.3 imol), potassium carbonate (14.7 mg, 0.106 mmol) and quinuclidine (0.95 mg, 8.50 jirnol) in CH3CN (850 il) was degassed, blanketed under N2 and irradiated with blue LED for 16 h, Additional amounts of 3-difluorocyclobutanol (11.5 mg, 0.106 mmoi), (4,4- di-t-butyi-2,2-bipyridine)bi s[3 , 5-difiuoro-2–[5-trifiuoromethyi-2-pyridinyl-kappan)phenyl kappaciiridiurn(1II) hexafluorophosphate (0.87 mg, 0.850 lrnol), nickei(II) bromide ethyleneglycol dimethyl ether complex (1.3 mg, 4.25 jimol), (1.1 mg,4.25 umol), potassium carbonate (14.7mg, 0.106 mrnoi) and quinuclidine (0.95 mg, 8.50 FIrnol) were added, the reaction mixture was degassed, blanketed under N2 and irradiated with blue LED for additional 16 h w/ air cooling. The reaction mixture was quenched with TFA, concentrated, suspended in DMF, filtered and purified by reverse phase HPLC to afford Example 360 (4.3 mg,10 % yield). MS ES1) ith: 497.9 (M+H). iHri4R (500 MHz, DMSO-d6) oe ppm ). 28 (br d,J=7.6 Hz, IH), 8.48 (br d, J7.6 Hz, 1H), 8.31 8.24 (rn, IH), 8.21 (s, IH), 8.16 (dd, J=7.5, 1.7Hz. HI), 7.69 (hr s, 1H), 7.59 (hr s, IH), 710 (dd, J=7.3, 5.2 Hz. 1EI), 6.99 (hr s, 1H), 6.82 (bid,J=7.3 Hz, IH), 5.23 (quin, J=7.2 Hz, IH), 4.90 (hr s, III), 4.43 .- 4.31 (rn, 1H), 3.28 (hr d, J=4.6Hz, IH), 281 – 270 (m, 2F), 2.70 2.59 (m, IH), 239 – 2.32 (in, 1H). 2.27 (hr dd, J1 1.3, 7.3Hz, IH), 2.21 (br d, J=4.0 Hz, 1H), 2.20 2.12 (m, 2H). Analytical HPLC RI? = 1.240 mm(Method A) and 1.554 mm (Method B), purity 95%.
The synthetic route of 637031-88-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
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