Potassium Cyanide → (1-[(tert-butoxycarbonyl)oxy]-6-methoxy-1H-indazol-3-yl)acetonitrile

HRID 1921262Notes

Reaction equation

HRID 1921262 reaction equation
[C-:1]#[N:2].[K+].[C:4]([O:8][C:9]([O:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:23]Br)=[N:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C(O)C>[C:4]([O:8][C:9]([O:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([CH2:23][C:1]#[N:2])=[N:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 231171601-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-bromomethyl-1H-indazole

Product 1

HCID 23117149(1-[(tert-butoxycarbonyl)oxy]-6-methoxy-1H-indazol-3-yl)acetonitrileYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

KCN (5.73 g, 88 mmol) in 23 ml of H2O was added dropwise at 0° C. to 1-[(tert-butoxycarbonyl)oxy]-6-methoxy-3-bromomethyl-1H-indazole (10.5 g, 30.08 mmol) in 80 ml of ethanol and stirred at room temperature for 1 h30. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was dried over Na2SO4. Concentration and precipitation in diisopropyl ether gave the expected product (4.42 g, 50% as solid).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationConcentration and precipitation in diisopropyl ether

Sources & evidence

ORD record
ord-970586ed9c1e4deca489af392aab1d60
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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