HCID 20611468, compound → Oxindole

HRID 983147Notes

Reaction equation

HRID 983147 reaction equation
FC(F)(F)C1C=C([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][C:12](=[O:18])[NH:13]3)C=CC=1.C[C@H]1N[C@@H](C)CN(C(C2C=C(C)NC=2C=O)=O)C1>C(O)C.N1CCCCC1>[NH:13]1[C:14]2[C:10](=[CH:9][CH:17]=[CH:16][CH:15]=2)[CH2:11][C:12]1=[O:18]

Participants

5

Reactant 2

HCID 20611468HCID 20611468, compoundHCID 225619054-(3-Trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 321710OxindoleYield 278.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(3-trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one (56.8 mg, 0.25 mmol) and 3-[(cis)3,5-dimethyl-piperazine-1-carbonyl]-5-methyl-1H-pyrrole-2-carbaldehyde (62.3 mg, 0.26 mmol) in ethanol (2 mL) was added piperidine (3 drops). The reaction mixture was stirred at room temperature for three days. A yellow solid product was precipitated out, filtered, washed by ethanol for three times, and dried under high vacuum to provide pure product 3-[3-((cis)-3,5-dimethyl-piperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-ylmethylene]-4-2-trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one as a yellow solid (92.7 mg, 73%).

Workup

  1. customA yellow solid product was precipitated out
  2. filtrationfiltered
  3. washwashed by ethanol for three times
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-56693a91e57c48eab3288a19d4d0b1a4
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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