* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Description 2; Methyl 3-iodo-2-pyridinecarboxylate (D2); A mixture of D1 (3.0 g, 0.012 mol) and c.H2SO4 (2 ml) in MeOH (100 ml) was heated at 65° C. for 18 h. After this period, solvents were evaporated in vacuo and the residue basified with solid NaHCO3. The residue was then extracted with EtOAc (3.x.100 ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.2 g, 70percent). deltaH(CDCl3, 250 MHz) 4.01 (3H, s), 7.13 (1H, dd), 8.29 (1H, dd), 8.64 (1H, dd). MS (ES): C7H61NO2 requires 263. found 264 (MH+)
70%
Description 2; Methyl 3-iodo-2-pyridinecarboxylate (D2); A mixture of D1 (3.Og, 0.012mol) and CH2SO4 (2ml) in MeOH (100ml) was heated at65°C for 18 h. After this period, solvents were evaporated in vacuo and the residue basified with solid NaHCO3. The residue was then extracted with EtOAc (3x100ml). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.2g, 70percent). deltaH (CDCI3, 250MHz) 4.01 (3H, s), 7.13 (1 H, dd), 8.29 (1H, dd), 8.64 (1H, dd). MS (ES): C7H6INO2 requires 263; found 264 (MH+)
Example 503-[4-Chloro-3-[[(2-tricyclo[3.3.1.13'7]dec-l-ylethyl)amino]carbonyl]phenyl]-2-pyridinecarboxylic acidCIa) 3-Iodo-2-pyridinecarboxylic acid, methyl esterButyllithium (32 mL, 2.5 M in hexanes) was added dropwise over 10 minutes to a solutionof 2,2,6,6-tetramethylpiperidine (10.2 mL) in tetrahydrofuran (100 mL) at-7 8 °C undernitrogen. The mixture was stirred at -78 °C for 15 minutes and then picolinic acid (2.4 g)was added portionwise over 10 minutes. After a further 10 minutes at -78 °C the mixturewas allowed to warm to 0 °C and stirred under nitrogen for 30 minutes. The reactionmixture was then added dropwise over 15 minutes to a solution of iodine (15 g) intetrahydrofuran (100 mL) at 0 °C. This was then allowed to warm to room temperature andstirred for 1 hour before water (20 mL) was added. The mixture was evaporated to drynessto leave a black oil. Dichloromethane (50 mL) was added and the mixture was cooled to 0°C. A^JV-Dimethylformamide (1 drop) and oxalyl chloride (4 mL) were added. The reactionwas allowed to warm to room temperature and stirred under nitrogen for 2 hours, thenevaporated to dryness. The residue was dissolved hi dichloromethane (20 mL) and thenmethanol (20 mL) was added. The mixture was then stirred for 10 minutes before beingevaporated to afford the sub-title compound as an oil (1.0 g) which was used in the nextstep without purification.MS: APCI(+ve) 264 (M+H4").
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
