Sodium Cyanide → HCID 59334572, compound

HRID 1639870Notes

Reaction equation

HRID 1639870 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH:12]1[CH2:14][CH:13]1[CH2:15][NH:16][C:17](=[O:19])[CH3:18].[C-:20]#[N:21].[Na+]>CN1CCCC1=O.C(OCC)(=O)C.[Ni](Br)Br>[C:20]([C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH:12]1[CH2:14][CH:13]1[CH2:15][NH:16][C:17](=[O:19])[CH3:18])#[N:21]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 59334491HCID 59334491, compound

Product 1

HCID 59334572HCID 59334572, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 278492Nickel(II) bromideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of N-{[2-(5-bromo-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (200 mg, 0.621 mmol) obtained in Example 29 in N-methylpyrrolidinone (3 mL) were added nickel(II) bromide (136 mg, 0.621 mmol) and sodium cyanide (61 mg, 1.241 mmol), and the mixture was stirred at 180° C. for 40 min using microwave. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) and recrystallization (ethyl acetate/hexane) to give the title compound (52 mg, yield 31%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23323cdae47c4b4dad84436e440d95d4
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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