Electric Literature of 10297-05-9, These common heterocyclic compound, 10297-05-9, name is 1-Chloro-4-iodobutane, 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.
EXAMPLE 1503-(2-isopropylphenyl)-5-(4-morpholin-4-ylbutoxy)-l -(3-( 1 -naphthyloxy)propyl)- 1 H-indole-2-carboxylic acidA mixture of EXAMPLE 149A (36 mg), l-chloro-4-iodobutane (0.043 ml) and cesium carbonate (116 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature overnight. The inorganic salt was filtered off. To the N,N-dimethylformamide solution was added morpholine (0.2 ml) and the resulting mixture was heated at 600C for 5 hours. The reaction mixture was concentrated and the residue was purified by RPHPLC (mobile phase: 10percent-100percent acetonitrile in 0.1percent TFA aqueous solution during 60 min) on a C18 column to give ethyl 3-(2-isopropylphenyl)-5-(4-morpholinobutoxy)-l-(3-(naphthalen- l-yloxy)propyl)-lH-indole-2-carboxylate. This ester was hydrolyzed with aqueous NaOH in a mixture of tetrahydrofuran and methanol to provide the title compound. 1H NMR (400 MHz, dimethyl sulfoxide-d6) ? 9.52 (s, IH), 8.20 (d, J=8.29Hz, IH), 7.87 (d, J=7.98Hz, IH), 7.59 (d, J=8.90Hz, IH), 7.43-7.57 (m, 3H), 7.30-7.43 (m, 3H), 7.14-7.23 (m, IH), 7.06 (d, J=7.36Hz, IH), 6.89 (dd, J=9.05, 2.30Hz, IH), 6.85 (d, J=7.67Hz, IH), 6.43 (d, J=2.45Hz, IH), 4.88 (t, J=7.21Hz, 2H), 4.15 (t, J=5.83Hz, 2H), 3.89-4.03 (m, J=I 1.97Hz, 2H), 3.75-3.89 (m, 2H), 3.55-3.70 (m, 2H), 3.07-3.17 (m, 2H), 3.02 (s, br, 2H), 2.61-2.78 (m, 2H), 2.23-2.45 (m, 2H), 1.60-1.85 (m, 4H).
The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ABBOTT LABORATORIES; WO2008/130970; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com