HCID 9881292, compound → HCID 59810835, compound

HRID 2240160Notes

Reaction equation

HRID 2240160 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]1

Participants

4

Reactant 2

HCID 9881292HCID 9881292, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59810835HCID 59810835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. stirringThe reaction was stirred at −78° C. for 1 hour
  2. customquenched by addition of 100 mL of saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with 3×50 mL of ethyl acetate
  4. dry with materialthe combined organic fractions were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-05c1ef57ba75460ea4113fa3be3a5e17
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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