2-(3-Butynyloxy)tetrahydro-2H-pyran → HCID 71252922, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5 M) (0.624 mL, 1.559 mmol) was added to a solution of 2-(3-butynyloxy)tetrahydro-2H-pyran (0.244 mL, 1.559 mmol) in THF (10 mL) at −78° C. The solution was stirred 1 h at this temperature before warming to 0° C. for 30 min at which time it was slowly added by syringe to a solution of 2-(tert-butylamino)-6-(2-methyl-6-(pyrrolidine-1-carbonyl)phenyl)quinoline-3-carbaldehyde (0.324 g, 0.780 mmol) in THF (10 mL) cooled to −78° C. The resulting dark solution was stirred 10 min at this temperature before warming to 0° C. for 20 min. The reaction mixture was diluted with saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give (2-(2-(tert-butylamino)-3-(1-hydroxy-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynyl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as an orange oil.

Provenance & Evidence