Potassium Carbonate → 5,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine

HRID 1399780Notes

Reaction equation

HRID 1399780 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:13]=[C:12]2[N:14]=[CH:15][NH:16][C:11]2=[C:10]([Cl:17])[CH:9]=1.Br[CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[Cl:7][C:8]1[N:13]=[C:12]2[N:14]([CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH:15]=[N:16][C:11]2=[C:10]([Cl:17])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1378441-(Bromomethyl)naphthaleneHCID 59498025,7-dichloro-1H-imidazo[4,5-b]pyridine

Product 1

HCID 896475365,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridineYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (798 mg, 5.77 mmol) was added to a solution of 5,7-dichloro-1H-imidazo[4,5-b]pyridine (350 mg, 1.862 mmol) (5,7-dichloro-3H-imidazo[4,5-b]pyridine, obtained as described in example 1) in N,N-Dimethylformamide (DMF) (6.5 mL) and the mixture was stirred for 25 min. 1-(bromomethyl)naphthalene (576 mg, 2.61 mmol) was then added and the reaction mixture was stirred at rt overnight. The mixture was poured onto water and the precipitate formed was collected by filtration. The residue was purified on silica gel (15 to 30% EtOAc in hexanes) to give 5,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (160 mg, 0.488 mmol, 26.2% yield) as a light yellow powder. MS (ES+) m/e 328 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67 (s, 1H), 8.25 (d, J=8.08 Hz, 1H), 7.97-8.03 (m, 1H), 7.92 (d, J=8.34 Hz, 1H), 7.66-7.70 (m, 1H), 7.56-7.66 (m, 2H), 7.41-7.49 (m, 1H), 7.11 (d, J=6.32 Hz, 1H), 6.00 (s, 2H)

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. additionThe mixture was poured onto water
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. customThe residue was purified on silica gel (15 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f944008dce5b40b8bb6f320ce4a5e714
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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