Potassium Cyanide → HCID 9943216, compound

HRID 428726Notes

Reaction equation

HRID 428726 reaction equation
C(C1C=C2C(=CC=1)NC(=O)/C/2=C\C1NC=CC=1)#C.[CH3:19][O:20][C:21]1[CH:25]=[CH:24][NH:23][C:22]=1/[CH:26]=[C:27]1\[C:28](=[O:42])[NH:29][C:30]2[C:35]\1=[CH:34][C:33]([C:36]#[C:37][Si](C)(C)C)=[CH:32][CH:31]=2.[C-]#N.[K+]>C(O)C.O1CCCC1.O.[N+]([O-])([O-])=O.[Ag+]>[C:36]([C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:42])/[C:27]/2=[CH:26]\[C:22]1[NH:23][CH:24]=[CH:25][C:21]=1[O:20][CH3:19])#[CH:37]

Participants

8

Reactant 3

HCID 9032Potassium CyanideHCID 9797871HCID 9797871, compoundHCID 9813420HCID 9813420, compound

Product 1

HCID 9943216HCID 9943216, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

This compound was also prepared in a manner analogous to the preparation of (Z)-1,3-dihydro-5-ethynyl-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one in Example 82 above. In this example, (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-(trimethylsilyl)ethynyl-2H-indol-2-one (100 mg, 0.3 mmol) (Example 92) in 5 mL ethanol and 1.5 mL tetrahydrofuran was treated with silver nitrate (0.112 g, 0.6 mmol) in 1.5 mL ethanol and 0.5 mL water, followed by potassium cyanide (218 mg, 3.35 mmol) in 1 mL water to give 70 mg (89%) of (Z)-1,3-dihydro-5-ethynyl-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (61 mg after recrystallization).

Sources & evidence

ORD record
ord-1a5a246644e246a284ca09730c39a826
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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