Potassium Carbonate → 2-(azetidin-1-yl)-1H-indole

HRID 1721379Notes

Reaction equation

HRID 1721379 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10](CC=O)[CH2:9]1)=O)(C)(C)C.N1([C:20]2[CH:25]=[CH:24][C:23]([NH:26]N)=[CH:22][CH:21]=2)C=NC=N1.[C:28]([O-])([O-])=O.[K+].[K+]>OS(O)(=O)=O>[N:8]1([C:6]2[NH:26][C:23]3[C:24]([CH:28]=2)=[CH:25][CH:20]=[CH:21][CH:22]=3)[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 103298204-(1,2,4-Triazol-1-yl)phenylhydrazineHCID 53415272tert-Butyl 3-(2-oxoethyl)azetidine-1-carboxylate

Product 1

HCID 867494502-(azetidin-1-yl)-1H-indoleYield 39%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-tert-Butyloxycarbonyl-3-formylmethylazetidine (0.4 g, 2.01 mmol) was added to a solution of 4-(1,2,4-triazol-1-yl)phenylhydrazine (0.35 g, 2.01 mmol) in 4% H2SO4 (50 ml) and the mixture refiuxed for 16h. The mixture was then cooled to room temperature, basified (K2CO3) and extracted with n-butanol (5 x). The crude product obtained was chromatographed on silica-gel eluting with CH2Cl2 /MeOH/NH3 (20:8:1) to give the title-azetidinylindole (0.186 g, 39%); δ (360 MHz, CD3OD) 3.80-3.88 (4H, m, 2 of CH2 of azetidine), 4.12-4.23 (1H, m, CH), 7.23 (1H, s, Ar--H), 7.39 (2H, s, Ar--H), 7.65 (1H, d, J=2.5 Hz, Ar--H), 8.04 (1H, s, Ar--H), 8.89 (1H, s, Ar--H).

Workup

  1. extractionextracted with n-butanol (5 x)
  2. customThe crude product obtained
  3. customwas chromatographed on silica-gel
  4. washeluting with CH2Cl2 /MeOH/NH3 (20:8:1)

Sources & evidence

ORD record
ord-08df9d488bd24f8c9123045b24042b52
Source dataset
uspto-grants-1996_04
Patent number
US05510362

Reaction notes

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