Hydrazine → Oxindole

HRID 2355776Notes

Reaction equation

HRID 2355776 reaction equation
F[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=O.NN>C(O)CO>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:7][C:8]1=[O:11]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 5864187-Fluoroisatin

Product 1

HCID 321710Oxindole

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

In still a further embodiment, a process is provided for preparing 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile including reacting 7-fluoro-1H-indole-2,3-dione and aqueous hydrazine in ethylene glycol to form the 2-oxindole; alkylating the 2-oxindole at the 3-position; brominating the alkylated 2-oxindole; reacting the brominated 2-oxindole with 5-[1,3,6,2]dioxazaborocan-2-yl-1-methyl-1H-pyrrole-2-carbonitrile, sodium carbonate, and PdCl2(PPh3)2; removing residual PdCl2(PPh3)2 or a by-product thereof using N-acetyl-L-cysteine; and isolating 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile. See, Scheme 6.

Sources & evidence

ORD record
ord-c26051d3cc1849bc907e36e1ed2cc99b
Source dataset
uspto-grants-2010_07
Patent number
US07754895B2

Reaction notes

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