Tetrahydrofuran → HCID 57423219, compound

Temperature

-70 °C

n-BuLi 2.5 M in hexane (1.2 mL, 3 mmol, 3 eq) was added at −70° C. to a solution of the product from the previous step, N-{2-[(6-bromo-2-pyridinyl)oxy]ethyl}-N,N-dimethylamine (245 mg, 1 mmol) in dry THF (10 mL). The reaction mixture was stirred at −70° C. for 1 h 30 min. Ethyl formate (freshly distilled over P2O5) was added at −70° C., and the reaction mixture was stirred at −70° C. for 2 hours. The reaction was quenched with addition of water. The reaction mixture was extracted with 3 portions of DCM. Combined organic phase were dried with MgSO4, filtrated and evaporated to give the desired product, 6-[2-(dimethylamino)ethoxy]-2-pyridinecarbaldehyde (192 mg, 0.988 mmol, 99%).

1. distillationEthyl formate (freshly distilled over P2O5)
2. additionwas added at −70° C.
3. stirringthe reaction mixture was stirred at −70° C. for 2 hours
4. customThe reaction was quenched with addition of water
5. extractionThe reaction mixture was extracted with 3 portions of DCM
6. dry with materialCombined organic phase were dried with MgSO4
7. filtrationfiltrated
8. customevaporated

ORD record

ord-0f14d94745fa4667b6e6b665523b66f2

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415480B2