1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde → 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-ol

HRID 218126

Reaction equation

HRID 218126 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([OH:18])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 579436121-(4-fluorophenyl)-1H-indazole-5-carbaldehydeHCID 178418816HCID 178418816, compound

Product 1

HCID 670061961-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)-1H-indazole-5-carboxaldehyde (100 mg, 0.416 mmol, from experimental 1(e)) in 5 mL of THF was added a solution of 2.0M isobutylmagnesium bromide in THF (0.5 mmol) dropwise. After 1 hr, the reaction was quenched with sat. NH4Cl and extracted with 2× EtOAc. The EtOAc extracts were dried over MgSO4, filtered, and concentrated by rotary evaporator to give 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-ol. MS found: (M+H)+=299.

Workup

  1. customthe reaction was quenched with sat. NH4Cl
  2. extractionextracted with 2× EtOAc
  3. dry with materialThe EtOAc extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-10ee93cb563d4ab6bac8774f9f4ac926
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Linked notes

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