Potassium Cyanide → (Z)-1,3-dihydro-4-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 1069699Notes

Reaction equation

HRID 1069699 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:9]1\[C:10](=[O:24])[NH:11][C:12]2[C:17]\1=[C:16]([C:18]#[C:19][Si](C)(C)C)[CH:15]=[CH:14][CH:13]=2.[C-]#N.[K+]>CCO.O.[N+]([O-])([O-])=O.[Ag+]>[C:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1/[C:9](=[CH:8]/[C:4]1[NH:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1])/[C:10](=[O:24])[NH:11]2)#[CH:19]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 59970995(Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-(2-trimethylsilyl-ethynyl)-2H-indol-2-one

Product 1

HCID 59970997(Z)-1,3-dihydro-4-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Using Method K above, a solution of (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-(2-trimethylsilyl-ethynyl)-2H-indol-2-one (1.3 g, 3.86 mmol) (from Step 1 above) in EtOH (80 mL) was treated with AgNO3 (1.46 g, 8.59 mmol) in ethanol (5 mL) and water (15 mL) at room temperature for 1 h followed by KCN (2.71 g, 41.6 mmol) in water (10 mL) to give (Z)-1,3-dihydro-4-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 1.02 g, 100%).

Sources & evidence

ORD record
ord-d0887b66133046f2865d9f92d2bcb033
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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