Sodium Iodide → HCID 58182714、化合物

温度

120 °C

The mixture of 6-amino-5-bromonicotinonitrile (3.315 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq), and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq) in anhydrous dioxane (40 mL under nitrogen atmosphere was stirred at 120° C. for 20 hours. The mixture was cooled to room temperature then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the crude solid residue was subject to a column chromatography started first with EtOAc-Hex (1:5 to 1:1) followed by MeOH—CHCl3 (1:100 to 1:20). Product containing fractions were all collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:4) yielding 3-iodo-5-isocyanopyridin-2-amine as an off-white solid in the amount of 2.75 g upon filtration.

1. temperatureThe mixture was cooled to room temperature
2. customthen partitioned between ethyl acetate and aqueous ammonium chloride
3. customThe organic layer was isolated
4. washfurther washed with saturated aqueous sodium bicarbonate, brine
5. dry with materialdried with anhydrous sodium sulfate
6. customThe upper solution was decanted
7. concentrationconcentrated
8. additionProduct containing fractions
9. customall collected
10. concentrationconcentrated
11. customThe solid residue was triturated with EtOAc-Hex (1:4)

ORDレコード

ord-7e1ee5ac571f4c2ca06910a31bacfc15

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09359336B2