Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine-2-carbaldehyde

To a solution of 2 (200 mg, 1.18 mmol) in dry THF (10 mL) at −78° C. was added n-BuLi (0.57 mL, 1.42 mmol, 2.5 M solution in hexanes) and the resultant suspension was stirred for 20 min. Dry DMF (0.5 mL, excess) was added and the reaction mixture was stirred for an additional 2 hrs. The reaction mixture was quenched with methanol at −78° C. and water was added. The mixture was extracted with EtOAc and the organic extracts were combined, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the resultant yellow solid was triturated with hexane to afford 14 (250 mg, 100% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 10.2 (s, 1H), 8.78 (d, J=5.1 Hz, 1H), 8.61 (s, 1H), 7.78 (d, J=5.1 Hz, 1H).

1. customThe reaction mixture was quenched with methanol at −78° C.
2. additionwater was added
3. extractionThe mixture was extracted with EtOAc
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customThe solvent was removed under reduced pressure
7. customthe resultant yellow solid was triturated with hexane

ORD record

ord-61434f71986b4ec494bfc0c244d0f67e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470850B2