Synthetic Route of 699-03-6, A common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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.
General procedure: To an oven dried 10 mL screw cap vial equipped with a stir-bar and charged with amine 1a (0.5 mmol) was added aldehyde 2a (84 mg, 1.5 equiv) and toluene (0.2 mL) and the mixture was stirred for 5 min at room temperature. Thereafter, heteroarene 3a (88 mg, 1.2 equiv) and CuCl (20 mol%) were added and the vial was sealed with a Teflon cap. The reaction mixture was irradiated for 50 min at a preselected temperature of 140 oC, with a maximum irradiation power of 200 W. After completion of the reaction, Oxadiazole 3a (0.5 mmol), Pd(OAc)2 (10 mol%), PPh3 (20 mol%), Cs2CO3 (2 equiv) and toluene (2 mL) was added and the reaction mixture was again irradiated under microwave for 40 min at 120 oC, 200 W. Thereafter, the resulting mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude sample was purified by silica gel column chromatography (15-25% ethyl acetate in heptane) to obtain 7a (174 mg, 69% yield).White solid, m.p. 146-148 oC, yield 69 %, 1H NMR (300 MHz, CDCl3): 8.19-8.03 (m, 6H), 7.61-7.44 (m, 8H), 3.82-3.71 (m,2H), 3.56 (d, J = 13.95 Hz, 1H), 2.38-2.26 (m, 4H), 2.20-2.08 (m, 1H), 1.89-1.78 (m, 1H), 1.73-1.62 (m, 2H), 1.44-1.16 (m,4H), 1.10-0.84 (m, 2H). 13C NMR (75 MHz, CDCl3): 164.7, 164.6, 164.4, 143.3, 131.7 (2), 129.3, 129.1, 129.0, 127.0, 126.9,124.0, 123.9, 122.7, 64.1, 58.6, 37.6, 37.5, 30.6, 30.1, 26.4, 25.8, 25.7. HRMS (EI): calcd for C31H31N5O2: 505.2478, found:505.2451.
The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Vachhani, Dipak D.; Sharma, Abhishek; Van Der Eycken, Erik; Angewandte Chemie – International Edition; vol. 52; 9; (2013); p. 2547 – 2550; Angew. Chem.; vol. 125; 9; (2013); p. 2607 – 2610,4;,
Bromide – Wikipedia,
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