Piperidine → Imidazolyl indolinone

HRID 413727

Reaction equation

HRID 413727 reaction equation
C([C:3]1[NH:4][CH:5]=[C:6](C=O)[N:7]=1)C.C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.N1CCCCC1.[NH:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][C:38]1=[O:46]>CN(C=O)C>[NH:4]1[CH:5]=[CH:6][N:7]=[C:3]1[N:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][C:38]1=[O:46]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 945242-Chlorotrityl chlorideHCID 321710OxindoleHCID 178437699HCID 178437699, compound

Product 1

HCID 23177814Imidazolyl indolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-ethyl-4-formylimidazole attached to 2-chlorotrityl resin (4, 78 mg, 0.052 mmol based on 0.67 mmol/g loading), DMF (0.9 ml) and piperidine (0.1 ml) was gently stirred for 45 min. at ambient temperature, afterwhich was added 2-indolinone (5, 70 mg, 0.523 mmol). The resultant mixture was gently stirred and heated at 80° C. for 20 h. The resin was filtered and washed with 30 ml each of acetone, water, dichloromethane, methanol, and another portion of acetone. Finally, the resin was air dried for 20 min.

Workup

  1. temperatureheated at 80° C. for 20 h
  2. filtrationThe resin was filtered
  3. washwashed with 30 ml each of acetone, water, dichloromethane, methanol
  4. customdried for 20 min.

Sources & evidence

ORD record
ord-cf0e67eac901434eaae9842178cdff62
Source dataset
uspto-grants-2003_05
Patent number
US06569868B2

Linked notes

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