3-Pyridinecarboxaldehyde → 1-cyclopropyl-5-methoxy-2-(pyridin-3-yl)-1H-benzimidazole

HRID 1048986Notes

Reaction equation

HRID 1048986 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]([NH2:13])=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:1]1([N:4]2[C:5]3[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=3[N:13]=[C:20]2[C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68053640HCID 68053640, compound

Product 1

HCID 666929981-cyclopropyl-5-methoxy-2-(pyridin-3-yl)-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N1-cyclopropyl-4-methoxy-benzene-1,2-diamine (0.2 g, 0.0011 mol) and pyridine-3-carbaldehyde (0.12 g, 0.0011 mol) in DMF (5 ml) and H2O (2 ml) was added OXONE® monopersulphate (0.81 g, 0.00132 map. Reaction mass was stirred at room temperature for 3 h. The reaction mixture was basified with 10% K2CO3 solution to pH˜8-10 and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford the crude compound which was purified by column chromatography to obtain title compound 1-cyclopropyl-5-methoxy-2-(pyridin-3-yl)-1H-benzimidazole (376). 1H NMR (400 MHz, DMSO-d6), δ: 9.16 (s, 1H), 8.70 (s, 1H), 8.37 (d, J=8.8 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.23 (s, 1H), 6.96 (d, J=8.8 Hz, 1H), 3.80 (s, 3H), 1.10 (d, J=6.4 Hz, 2H), 0.64 (s, 2H). MS (M+1): 266.1, Purity 98.98%.

Workup

  1. customReaction mass
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude compound which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c0744489535e4762bf8bea45a681ee0f
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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