Electric Literature of 124700-41-0,Some common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, molecular formula is C7H4FIO2, 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.
Intermediate 1C: (3,4-Dihydroisoquinolin-2(lH)-yl)(2-fluoro-5-iodophenyl)methanone[00165] To a suspension of 2-fluoro-5-iodobenzoic acid (Aldrich, 5.27 g, 19.8 mmol) in CH2CI2 (35.0 mL) was added oxalyl chloride (14.9 mL, 29.7 mmol, 1M solution in CH2CI2) followed by 2 drops of DMF via syringe. Gas evolution was initiated and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was then quenched with sat. aq. NH4CI solution and extracted with EtOAc (3 x). The combined organic extracts were dried over Na2S04, filtered and concentrated in vacuo to give crude 2-fluoro-5-iodobenzoyl chloride which was used directly in the next step.[00166] The crude product obtained above was dissolved in CH2CI2 (49.6 mL) and cooled to 0 C. To the solution were added 1,2,3,4-tetrahydroisoquinoline (2.7 mL, 21.8 mmol) followed by 2,6-lutidine (4.6 mL, 39.7 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was washed IN HC1 (2 x) and the organic layer was extracted with CH2CI2 (2 x). The combined organic extracts were washed with sat. aq. NaCl solution and dried over a2S04. Filtration and concentration in vacuo provided the title compound (7.55 g, 95%) as a viscous, yellow oil. XH NMR (CDCI3, 1.5: 1 mixture of amide rotamers) delta 7.78-7.66 (m, 2H), 7.26-7.12 (m, 3.5H), 6.98- 6.86 (m, 1.5H), 4.92 (s, 1.5H), 4.50 (br s, 0.5H), 3.65-3.52 (m, 1.5H), 3.04-2.95 (m, 1H), 2.92-2.82 (m, 1.5H); MS(ESI+) m/z 382.1 (M+H)+.
The synthetic route of 124700-41-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; CAI, Zhen-wei; TEBBEN, Andrew J.; PEREZ, Heidi L.; ZHANG, Liping; SCHROEDER, Gretchen M.; WEI, Donna D.; WO2012/162365; (2012); A1;,
Iodide – Wikipedia,
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