Piperidine → HCID 178517065, compound

HRID 1615373Notes

Reaction equation

HRID 1615373 reaction equation
N1CCCCC1.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=[O:16].[I:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=O)[CH:25]=2)[NH:20][N:19]=1>CCO>[I:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=[C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[NH:7][C:8]3=[O:16])[CH:25]=2)[NH:20][N:19]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 178519380HCID 178519380, compound

Product 1

HCID 178517065HCID 178517065, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Piperidine (0.01 mL, 0.1 mmol) was added to a suspension of oxindole (72 mg, 0.54 mmol) and 3-iodo-1H-indazole-5-carbaldehyde (146 mg, 0.54 mmol) in EtOH (10 mL). On heating to 75° C., the suspended solid dissolved, and a new precipitate formed. Heating was continued at 75° C. for 14 hrs. After the mixture was cooled to room temperature, suction filtration and rinsing with EtOH (4×2 mL) gave 3-((3-iodo-1H-indazol-5-yl)methylene)indolin-2-one (yellow solid, 131.9 mg, 63%). 1H NMR (400 MHz, d6-DMSO) δ 13.75 (br. s, 1H), 10.61 (br. s, 1H), 7.84 (s, 1H), 7.77 (m, 2H), 7.69 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.23 (m, 1H), 6.88 (d, J=8.0 Hz, 1H), 6.84 (m, 1H); MS ESI 388.0 [M+H]+, calcd for [C16H10IN3O+H]+ 388.0.

Workup

  1. dissolutionthe suspended solid dissolved
  2. customa new precipitate formed
  3. temperatureHeating
  4. temperatureAfter the mixture was cooled to room temperature
  5. filtrationsuction filtration
  6. washrinsing with EtOH (4×2 mL)

Sources & evidence

ORD record
ord-8fc7ed23009142899f7f1970977d06bb
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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