Iodine → HCID 86662407, compound

Temperature

-78 °C

7-Chlorofuro[2,3-c]pyridine (7.60 g, 49.7 mmol) was placed in a three-necked flask fitted with a thermometer and nitrogen inlet and then anhydrous tetrahydrofuran (150 mL) was added. The solution was cooled to −78° C. To this cold solution was added gradually 2 M LDA solution (32.3 mL, 64.6 mmol) by syringe and the resulting mixture was stirred for 2 h at −78° C. Then a solution of iodine (15.1 g, 59.5 mmol) in dry THF (100 mL) was added at −78° C. and the resulting mixture was allowed to warm to RT overnight. The reaction was quenched with aqueous sodium thiosulfate (75 mL) and diluted with ethyl acetate (150 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2×75 mL). All organic layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to give 13.7 g (99%) of the title compound as a brown solid. 1H NMR (300 MHz, CDCl3): δ 7.06 (s, 1H), 7.40 (d, J=6.0 Hz, 1 H), 8.17 (d, J=6.0 Hz, 1H).

1. customfitted with a thermometer and nitrogen inlet
2. temperatureto warm to RT overnight
3. customThe reaction was quenched with aqueous sodium thiosulfate (75 mL)
4. additiondiluted with ethyl acetate (150 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with ethyl acetate (2×75 mL)
7. washwashed with brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. customevaporated

ORD record

ord-0b04ca8204da446ea395bb72d6e76571

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2