3-Buten-2-ol → HCID 21931388, compound

Temperature

50 °C

Part A. To a mixture of 2-chloro-5-iodopyridine (6.76 g, 28.2 mmol) in 50 mL N,N-dimethylformamide was added 1-buten-3-ol (24.4 mL, 282.3 mmol), palladium acetate (0.64 g, 2.82 mmol), tetrabutylammonium chloride (0.79 g, 2.82 mmol), and sodium bicarbonate (5.94 g, 70.6 mmol). The resulting mixture was stirred at 50° C. for 5 hr, and then quenched with water (20 mL). Subsequently, the mixture was diluted with 20 mL of ethyl acetate and filtered through a pack of celite. The organic layer was separated from the filtrate, and the aqueous layer was further extracted with ethyl acetate. The organics were combined, washed with saturated NaCl solution, and dried over magnesium sulfate. Chromatography (on silica, ethyl acetate/hexane) afforded the desired 4-(6-chloropyridin-3-yl)butan-2-one intermediate in the form of a yellow oil (4.01 g, 77% yield). MS MH+ for C9H10ClNO: calc. 184, found 184.

1. customquenched with water (20 mL)
2. additionSubsequently, the mixture was diluted with 20 mL of ethyl acetate
3. filtrationfiltered through a pack of celite
4. customThe organic layer was separated from the filtrate
5. extractionthe aqueous layer was further extracted with ethyl acetate
6. washwashed with saturated NaCl solution
7. dry with materialdried over magnesium sulfate

ORD record

ord-8082f1cd21454ff7a57071e0827ded66

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119203B2