Pyrrole-2-carboxaldehyde → HCID 66675856, compound

HRID 422007Notes

Reaction equation

HRID 422007 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:8]=2)[NH:3]1.[NH:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=O>C(O)C.N1CCCCC1>[O:1]=[C:2]1[C:10](=[CH:25][C:21]2[NH:20][CH:24]=[CH:23][CH:22]=2)[C:9]2[C:4](=[CH:5][C:6]([NH:11][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 219257686-Benzamido-2-oxindole

Product 1

HCID 66675856HCID 66675856, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-amino-1,3-dihydro-indol-2-one (0.15 g, 1.0 mmol) in 2:1 CH2Cl2-1,4-dioxane mixture (30 ml) is added triethylamine (0.30 g, 3.0 mmol) and benzoyl chloride (0.14 g, 1.0 mmol). The reaction is stirred for 2 hours at room temperature, and then a saturated aqueous solution of NH4Cl is added. The precipitate is collected and washed with water to give crude N-(2-oxo-2,3-dihydro-1H-indol-6-yl)-benzamide. To a solution of this benzamide (20 mg, 0.079 mmol) and 1H-pyrrole-2-carbaldehyde (7.6 mg, 0.079 mmol) in ethanol (2 ml) is added 2 drops of piperidine. It is stirred at 80° C. for 4 hours and then cooled to room temperature. The precipitate is collected by vacuum filtration, washed with a small amount of cold ethanol and purified by HPLC(C18 column, eluted with CH3CN—H2O containing 0.05% TFA) to give the desired compound as an orange solid: 1H NMR (DMSO-d6) δ 6.34 (s, 1H), 6.80 (s, 1H), 7.33 (s, 1H), 7.39 (d, 1H, J=8.4 Hz), 7.53 (t, 2H, J=7.8 Hz), 7.57 (s, 1H), 7.59 (s, 1H), 7.61 (s, 1H), 7.64 (s, 1H), 7.96 (d, 2H, J=7.8 Hz), 10.29 (s, 1H), 10.94 (s, 1H), 13.23 (s, 1H); LC-MS: 330.1 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate is collected by vacuum filtration
  3. washwashed with a small amount of cold ethanol
  4. custompurified by HPLC(C18 column
  5. washeluted with CH3CN—H2O containing 0.05% TFA)

Sources & evidence

ORD record
ord-60b6a77226e340a2b53745b2a3896ca2
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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