Water → 4-Pyrimidin-5-yl-1,3-dihydroindol-2-one

HRID 988135Notes

Reaction equation

HRID 988135 reaction equation
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[N:22]1[CH:27]=[C:26]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][NH:32]3)[CH:25]=[N:24][CH:23]=1.[OH2:37]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[N:24]1[CH:25]=[C:26]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH2:30][C:31](=[O:37])[NH:32]3)[CH:27]=[N:22][CH:23]=1

Participants

8

Reactant 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 221354894-pyrimidin-5-yl-1H-indole

Product 1

HCID 221354004-Pyrimidin-5-yl-1,3-dihydroindol-2-oneYield 75%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

Pyridinium tribromide (90% (Aldrich), 4 g, 11.22 mmol) was added portion-wise over 10 minutes to a suspension of 4-pyrimidin-5-yl-1H-indole (730 mg, 3.74 mmol) in 2-methyl-2-propanol (25 mL), ethanol (15 mL) and acetic acid (9 mL). The mixture was stirred at room temperature for 2 hours after which acetic acid (36 mL), water (1 mL) and zinc (3.2 g, 56.1 mmol) were added. Stirring was continued for 1.5 hours. Residual zinc dust was filtered and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (100 mL) overnight. The precipitate which formed was filtered, washed with water to remove zinc and pyridine salts and dried under high vacuum to give 595 mg (75%) of 4-pyrimidin-5-yl-1,3-dihydroindol-2-one as a light brown solid.

Workup

  1. additionwere added
  2. filtrationResidual zinc dust was filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated
  5. stirringthe syrupy residue was stirred in water (100 mL) overnight
  6. customThe precipitate which formed
  7. filtrationwas filtered
  8. washwashed with water
  9. customto remove zinc and pyridine salts
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-f20de53753ad4778936cf397d43d325a
Source dataset
uspto-grants-2003_10
Patent number
US06635640B2

Reaction notes

Loading…