TERT-BUTYL (2,6-DICHLORO-4-IODOPYRIDIN-3-YL)CARBAMATE synthesis

Yield:1044660-87-8 95%

Reaction Conditions:

Stage #1: tert-butyl 2,6-dichloropyridin-3-ylcarbamatewith n-butyllithium in tetrahydrofuran at -78; for 0.5 h;Inert atmosphere;
Stage #2: with iodine in tetrahydrofuran at -78; for 1 h;

Steps:

139 EXAMPLE 139 Preparation of Compound 335

[0596] To a solution of 335-1 (5.2 g, 20 mmol) in THF (30 mL) was added n- BuLi (16 mL, 20mmol, 2.5M) at -78 °C under N₂. After stirred at -78°C for 0.5 h, a solution of I? (5.1 g 20 mmol) in THF (25 mL) was added slowly. The mixture was stirred at -78 °C for 1 h. The reaction was quenched with water and extracted with ΕΛ (3 x 50 mL). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE:EA 10: 1 ) to give 335-2 (7.5 g. 95 %). +ES1-MS: m/z 388.9 [M+H]⁺.

References:

WO2015/26792,2015,A1 Location in patent:Paragraph 0596