Pyrrole-2-carboxaldehyde → HCID 71815639, compound

HRID 1844106Notes

Reaction equation

HRID 1844106 reaction equation
N1CCCC1.[CH3:6][O:7][C:8]1[CH:29]=[CH:28][C:11]([C:12]([NH:14][C:15](=[O:27])[NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][C:20](=[O:26])[NH:21]3)=[O:13])=[CH:10][CH:9]=1.[NH:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH:35]=O>C(O)C>[NH:30]1[CH:34]=[CH:33][CH:32]=[C:31]1/[CH:35]=[C:19]1\[C:20](=[O:26])[NH:21][C:22]2[C:18]\1=[C:17]([NH:16][C:15]([NH:14][C:12](=[O:13])[C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:29][CH:28]=1)=[O:27])[CH:25]=[CH:24][CH:23]=2

Participants

5

Reactant 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 31268PyrrolidineHCID 86699718HCID 86699718, compound

Product 1

HCID 71815639HCID 71815639, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A catalytic amount of pyrrolidine (0.001 mmol) was added to a solution of 4-methoxy-N-(2-oxoindolin-4-ylcarbamoyl)benzamide (1 mmol) and pyrrole-2-carbaldehyde (1.2 mmol) in ethanol (5 mL). The reaction was carried out using microwave (CEM, Discover) at 100° C. (200 W. Standard mode) for 15 mins. Crude product was precipitated after cooling to RT, which was collected by filtration, washed with ethanol and air dried. YD: 65.57%; mp: Charred at 290-295° C. 1H NMR (DMSO-d6) 200 MHz, δ: 3.859 (s, 3H), 6.342-6.363 (m, 1H), 6.722-6.731 (m, 1H), 6.748 (d, J=7.6 Hz, 1H), 7.101 (d, J=9.2 Hz, 2H), 7.160 (t, J=8.0 Hz, 1H), 7.354 (br, 1H), 7.436 (d, J=8.0 Hz, 1H), 8.043 (s, 1H), 8.126 (d, J=8.8 Hz, 2H), 10.894 (s, 1H), 11.028 (s, 2H), 13.376 (s, 1H). (C22H18N4O4.1/2H2O) C, H, N. ESI-MS: m/z 400.9 [M−H]−.

Workup

  1. customat 100° C.
  2. customfor 15 mins
  3. customCrude product was precipitated
  4. filtrationwhich was collected by filtration
  5. washwashed with ethanol and air
  6. customdried
  7. customCharred at 290-295° C

Sources & evidence

ORD record
ord-e6c850c42068493e92c30e49cc413913
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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