Dichloromethane → 2-(4,6-Dichloropyridin-2-yl)thiazole

To a 15 mL vial equipped with a stir bar was added 2,4,6-trichloropyridine (182 mg, 1.00 mmol) and Pd(dppf)Cl2 (73.2 mg, 0.100 mmol). The vial was sealed with a septum screwcap and was then placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (8.00 mL, 4.00 mmol). The vial was placed in a 60° C. heating block with stirring for 3 h. The reaction mixture was transfered to a separatory funnel and diluted with water (25 mL) and sat. aq. NaCl (“brine”, 25 mL). The mixture was extracted with EtOAc:Et2O (40 mL:20 mL). The organic phase was washed with brine (25 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford an orange solid. This material was subjected to silica gel chromatography (CH2Cl2:MeOH, 100:0 to 99:1) to afford 2-(4,6-dichloropyridin-2-yl)thiazole as a white solid (231 mg, 46%). 1H-NMR (400 MHz, CDCl3) δ 8.16 (d, J=1.8 Hz, 1H), 7.95 (d, J=3.3 Hz, 1H), 7.52 (d, J=3.0 Hz, 1H), 7.37 (d, J=1.8 Hz, 1H).

1. customTo a 15 mL vial equipped with a stir bar
2. customThe vial was sealed with a septum screwcap
3. customwas placed in a 60° C.
4. temperatureheating block
5. customThe reaction mixture was transfered to a separatory funnel
6. extractionThe mixture was extracted with EtOAc
7. washThe organic phase was washed with brine (25 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationthen concentrated in vacuo
11. customto afford an orange solid

ORDレコード

ord-96a790dea285473b9f8e7aad7f33b977

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09334279B2