Water → 4-Thiazol-2-yl-1,3-dihydroindol-2-one

HRID 1826714Notes

Reaction equation

HRID 1826714 reaction equation
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH:29]=[CH:30][NH:31]2.[OH2:36]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH2:29][C:30](=[O:36])[NH:31]2

Participants

8

Reactant 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 221354134-thiazol-2-yl-1H-indole

Product 1

HCID 221354394-Thiazol-2-yl-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 4

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

Procedure

Pyridinium tribromide (90% (Aldrich), 1.9 g, 5.34 mmol) was added portion-wise over 10 minutes to a suspension of 4-thiazol-2-yl-1H-indole (360 mg, 1.78 mmol) in 2-methyl-2-propanol (15 mL), ethanol (9 mL) and acetic acid (5 mL). The mixture was stirred at room temperature for 2 hours after which acetic acid (18 mL), water (1 mL) and zinc dust (1.5 g, 23.14 mmol) were added. Stirring was continued for 1.5 hours. Residual zinc dust was removed by filtration and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (50 mL) overnight. The solid which formed was filtered, washed with water to remove the zinc and pyridine salts and dried under high vacuum to give 4-thiazol-2-yl-1,3-dihydroindol-2-one.

Workup

  1. additionwere added
  2. customResidual zinc dust was removed by filtration
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated
  5. stirringthe syrupy residue was stirred in water (50 mL) overnight
  6. customThe solid which formed
  7. filtrationwas filtered
  8. washwashed with water
  9. customto remove the zinc and pyridine salts
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-c374d96abeb9498a8705c217a23d055f
Source dataset
uspto-grants-2006_05
Patent number
US07053086B2

Reaction notes

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