HCID 9881292, compound → HCID 59810835, compound
Reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[O:16])[CH:13]=3)[C:8]([CH2:17][CH3:18])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][Mg]Cl>O1CCCC1>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH:15]([OH:16])[CH3:19])[CH:13]=3)[C:8]([CH2:17][CH3:18])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxaldehyde (1.00 g, 4.13 mmol) in 40 mL of tetrahydrofuran under argon was cooled to −78° C. and with stirring treated with 3 mL of 3 M methylmagnesium chloride in tetrahydrofuran. The reaction was stirred at −78° C. for 1 hour, slowly warmed to room temperature overnight and then quenched by addition of 100 mL of saturated aqueous NH4Cl. The mixture was extracted with 3×50 mL of ethyl acetate and the combined organic fractions were dried over sodium sulfate and concentrated to give 1-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)ethanol as a yellow solid. The crude residue was not purified but used as such in the next step.