3-[(3R)-3-dimethylamino-pyrrolidin-1-ylcarbonyl]-5-methyl-1H-pyrrole-2-carbaldehyde → Oxindole

HRID 983083Notes

Reaction equation

HRID 983083 reaction equation
FC1C=CC([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:17])[NH:12]3)=CC=1.CN(C)[C@@H]1CCN(C(C2C=C(C)NC=2C=O)=O)C1>C(O)C.N1CCCCC1>[NH:12]1[C:13]2[C:9](=[CH:8][CH:16]=[CH:15][CH:14]=2)[CH2:10][C:11]1=[O:17]

Participants

5

Reactant 2

HCID 206114663-[(3R)-3-dimethylamino-pyrrolidin-1-ylcarbonyl]-5-methyl-1H-pyrrole-2-carbaldehydeHCID 225618524-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-one

Product 1

HCID 321710Oxindole

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4-fluoro-phenyl)-1,3-dihydro-indol-2-one (56.8 mg, 0.25 mmol) and 3-[3-(3R)-dimethylamino-pyrrolidine-1-carbonyl]5-methyl-1H-pyrrole-2-carbaldehyde (64.8 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-[3-(3R)dimethylamino-pyrrolidine-1-carbonyl]-5-methyl-1H-pyrrol-2-ylmethylene]44-fluoro-phenyl)-1,3-dihydro-indol-2-one as a yellow solid (63.9, 56%).

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-b36bd91842b94bda92b31722280804dd
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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