Sodium triacetoxyborohydride → 2-chloro-4,4-difluoro-1'-[[1-(3-fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]

Participants

Reaction Steps

To a solution of 2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine] (170 mg, 0.61 mmol) in dichloromethane (2.4 mL), 1-(3-fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazole-4-carbaldehyde (192 mg) is added. The mixture is stirred 10 min at room temperature. Then, sodium triacetoxyborohydride (268.3 mg) is added, and the reaction is stirred at room temperature overnight. The mixture is diluted with dichloromethane and quenched slowly with sodium bicarbonate (saturated solution). The organic phase is then extracted with more dichloromethane, decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. The residue is purified by reverse phase HPLC to give 67.9 mg of 2-chloro-4,4-difluoro-1′-[[1-(3-fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine]. MS (m/z): 527 (M+1).

Provenance & Evidence