Ethyl Acetate → HCID 68997699, compound

HRID 490096Notes

Reaction equation

HRID 490096 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[CH3:19].[C-:20]#[N:21].[Na+].C(OCC)(=O)C>CN1C(=O)CCC1.[Ni](Br)Br>[C:20]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[CH3:19])#[N:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 59262248HCID 59262248, compound

Product 1

HCID 68997699HCID 68997699, compound

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 5-bromo-3-methyl-N-(2-trimethylsilanylethoxymethyl)indazole 116 (0.5 g, 1.466 mmol) in NMP (10 mL) was added nickel bromide (0.321 g, 1.469 mmol) and sodium cyanide (0.144 g, 2.939 mmol). The reaction mixture was heated in a microwave reactor at 180° C. for 30 minutes. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to yield the desired 5-cyano-3-methyl-N-(2-trimethylsilanylethoxymethyl)indazole 117. (0.36 g, 1.254 mmol).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-90821c17fa164d5d8187c20db265c5c9
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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