3-Butyn-1-OL → HCID 10309452, compound

2-Bromo-N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 79, 0.100 g) was suspended in a mixture of triethylamine (2.5 mL) and DMF (0.5 mL). CuI (0.006 g), Pd(PPh3)2Cl2 (0.017 g), and then 3-butyn-1-ol (0.038 mL) were added. The mixture was stirred at room temperature for 30 min and then was partitioned between CH2Cl2 (10 mL) and water (10 mL). The aqueous layer was separated and was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with a sat. aq. ammonium chloride solution (10 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.035 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 242-243° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.51, 8.59, 7.41-7.32, 7.21, 5.01, 4.55, 3.92, 3.61, 2.67; MS (ESI+) m/z 385 (,M+H)+.

1. customwas partitioned between CH2Cl2 (10 mL) and water (10 mL)
2. customThe aqueous layer was separated
3. extractionwas extracted with CH2Cl2 (3×10 mL)
4. washThe combined organic layers were washed with a sat. aq. ammonium chloride solution (10 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
9. customfollowed by recrystallization from ethyl acetate

ORD record

ord-8a73ee19d06b45d999a9999cbd5b71e3

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878705B2