benzyl 3-(1-methyl-1H-benzimidazol-2-yl)azetidine-1-carboxylate → 2-(azetidin-3-yl)-1-methyl-1H-1,3-benzodiazole

HRID 1486755Notes

Reaction equation

HRID 1486755 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]1[CH2:14][N:13](C(OCC2C=CC=CC=2)=O)[CH2:12]1.[H][H]>CO.[Pd]>[NH:13]1[CH2:14][CH:11]([C:3]2[N:2]([CH3:1])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 89486757benzyl 3-(1-methyl-1H-benzimidazol-2-yl)azetidine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 894881762-(azetidin-3-yl)-1-methyl-1H-1,3-benzodiazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-3 (3.32 g, 10.33 mmol) in MeOH (52 mL) was subjected to 2 cycles of the evacuation/backfilling with nitrogen and then treated with 10% Pd/C (1.1 g). The evacuation/backfilling with nitrogen procedure was repeated two times and then the nitrogen atmosphere was exchanged for a hydrogen atmosphere by evacuation/backfilling with a balloon of hydrogen. After stirring for 3 h under hydrogen at room temperature, the reaction mixture was filtered through celite, and washed with additional MeOH (20 mL). The filtrate was concentrated to yield Intermediate 1 as brown solid. MS: m/z=188.2 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with additional MeOH (20 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ce098ffee9f4440a9010fbd602c7643d
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

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