반응 #574

반응 방정식

Clc1ccc(Br)c(Cl)n1

C1COCCN1

→

Clc1ccc(N2CCOCC2)c(C

용매

CC(C)(C)O

반응 조건

실험 절차

2011-05-18 r1 was checked by NMR and LC/MS: Vial a: 3-bromo-2,6-dichloropyridine (0.023 g, .1 mmol), morpholine (9.15 µl, 0.11 mmol), Pd2dba3 (1.831 mg, 2.00 µmol),4-(2,6-dichloropyridin-3-yl)morpholine (0.00 µg) were mixed in tBuOH (0.241 ml) in microwave vial. The vial was flushed with N2 and sealed and the mix was strd at rt. Vial b: As above, but in PhCF3. 1100:start 2011-05-19 0800: LC/MS: around 50% r1 in both vials. vial a: new peak at 1.53 min (20%), at 2.90 min (17%) and some small peaks as well. vial b: new peak at 1.54 min (32%), 2.61 min (25%) and at 2.90 min (5%) and some small peaks as well. MW/100 degr/20 min. LC/MS, pH3: vial a: 1.17 min: new peak (8-9%, not integrated); 2.11 min: new peak (31%), no right mass track. vial b: 1.17 min: new, small peak; 2.11 min: new peak (17%), no right mass track. The peak from the 2.11 peak is relatively higher in vial a than in b. ACS calculation: r1 has logD 3.60, product has logD 1.92. Any Br->H? Check of ret time of 2,6-diCl-pyridine (commercial ref. material): 1.86 min. NO such thing. at rt over night 2011-05-20 0800: LC/MS: around 50% r1 in both vials. MW/100 degr/20 min. LC/MS: vial a: 1.17 min (8%); 1.51 min (ca. 5%); 2.12 min (32%); 2.47 min (r1 peak; 38%) + other small peaks. vial b: 1.54 min (19%); 2.12 min (21%); 2.48 (24%); 2.90 min (11%). The crudes were mixed, concentrated and kept at rt over night. 2011-05-21 Passed thru Si-plug with MeOH. NMR on crude: very messy. Scrutiny of the arom. region did not show anything that seemed like the right product. Not taken further.

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