5-Bromopyridine-2-carbaldehyde → HCID 87194490, compound

Temperature

73 °C

To a solution of 5-bromo-2-formyl-pyridine (3.0 g, 16.1 mmol) in dry THF (95 mL), (S)-tert-butylsulfinamide (2.05 g, 16.9 mmol) was added at RT under argon. Then titanium tetra-isopropoxyide (7 mL, 33.9 mmol) was added drop wise. The reaction mixture was stirred at 73° C. (external temperature) for 2.5 h, and was allowed to cool down. The reaction mixture was slowly poured into a vigorously stirring mixture of ca. 200 mL of brine and ice. The slurry was filtered and washed with DCM. The organic layer was separated and the aqueous layer was extracted twice with DCM. The combined organic layers were washed with brine, dried over MgSO4, filtered, evaporated to give a brown solid. The product was triturated in cold ether and successive filtered solids were combined to give the title intermediate (3.66 g, 12.4 mmol, 77%). HPLC: EtRet=4.987 min; LC-MS: m/z 291.0 [M+H]+.

1. temperatureto cool down
2. additionThe reaction mixture was slowly poured into
3. stirringa vigorously stirring
4. filtrationThe slurry was filtered
5. washwashed with DCM
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted twice with DCM
8. washThe combined organic layers were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customevaporated
12. customto give a brown solid
13. customThe product was triturated in cold ether
14. filtrationsuccessive filtered solids

ORD record

ord-0612a5966a2249599ec77a2379b5e26b

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440693B2