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

HRID 1011479Notes

Reaction equation

HRID 1011479 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 h 30. 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-b952ceb660fd41b99443940072e48c7d
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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