Electric Literature of 61272-76-2, A common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, molecular formula is C6H5FIN, 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 64 4-(((2-tert-Butyl-5-fluoro-1H-indol-3-yl)methoxy)methyl)-N,N-dimethyl-1-phenylcyclohexanamine (one of two possible diastereomers) A mixture of Ain-13 (522 mg, 1.60 mmol), 4-fluoro-2-iodoaniline (Ian-04) (453 mg, 1.90 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-3-chloropyridyl palladium(II) chloride (PEPPSI, 109 mg, 0.16 mmol) and sodium carbonate (848 mg, 8.0 mmol) was evacuated for 30 min (oil pump). The mixture was then flushed with argon and absolute N,N-dimethyl formamide (5 ml, previously flushed for 1 h with argon) was added with a syringe via a Schlenk attachment. The reaction mixture was stirred for 18 h at 10° C., during the course of which the solution turned a dark brown colour. The reaction solution was then concentrated to small volume under vacuum, the residue was taken up repeatedly in toluene (3*30 ml) and concentrated to small volume again each time, then divided between water and ethyl acetate (50 ml each) and the phases were separated. The aqueous phase was extracted with ethyl acetate (2*50 ml), the combined organic phases were washed with 1 M sodium thiosulfate solution and saturated sodium chloride solution (50 ml each), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (948 mg) was purified by flash chromatography (38 g, 20*2.5 cm) with chloroform/methanol (1:5). Yield: 421 mg (60percent) Melting point: 51-53° C. 1H-NMR (DMSO-d6): 1.19-1.68 (m, 7H); 1.44 (s, 9H); 1.89 (s, 6H); 2.54-2.64 (m, 2H); 3.29-3.31 (m, 2H); 4.64 (s, 2H); 6.84 (dt, 1H, J=2.5, 9.6 Hz); 7.23 (dd, 2H, J=2.5, 10.2 Hz); 7.27 (d, 1H, J=4.7 Hz); 7.29-7.37 (m, 4H); 10.79 (s, 1H). 13C-NMR (DMSO-d6): 24.5; 30.3; 32.1; 33.2; 37.0; 37.4; 58.5; 63.2; 74.5; 102.2 (d, 1C, J=23 Hz); 106.6; 108.1 (d, 1C, J=26 Hz); 111.6 (d, 1C, J=0 Hz); 126.1; 126.5; 127.2; 129.8 (d, 1C, J=10 Hz); 130.7; 139.4; 147.5; 156.9 (d, 1C, J=231 Hz). Other C signals were unable to be identified.
The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com