Sodium Methoxide → 5-chloro-7-(methyloxy)-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine

HRID 1399781Notes

Reaction equation

HRID 1399781 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:10][C:5]2=[C:4](Cl)[CH:3]=1.[CH3:23][O-:24].[Na+]>CO.O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:10][C:5]2=[C:4]([O:24][CH3:23])[CH:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 896475365,7-dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 896479945-chloro-7-(methyloxy)-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridineYield 69.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5,7-Dichloro-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (150 mg, 0.457 mmol) and sodium methoxide (0.157 mL, 0.686 mmol) in Methanol (1.5 mL) were irradiated in a microwave oven for 1 h at 110° C. The mixture was diluted with water, the precipitate was collected, washed with water, dried to give 5-chloro-7-(methyloxy)-3-(1-naphthalenylmethyl)-3H-imidazo[4,5-b]pyridine (143 mg, 0.318 mmol, 69.6% yield) which was used as is in the next step. MS (ES+) m/e 324 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.36 (s, 1H), 8.24 (d, J=7.83 Hz, 1H), 7.95-8.03 (m, 1H), 7.91 (d, J=8.08 Hz, 1H), 7.60 (qd, J=7.20, 5.43 Hz, 2H), 7.44 (dd, J=8.21, 7.20 Hz, 1H), 7.02 (d, J=7.07 Hz, 1H), 6.99 (s, 1H), 5.93 (s, 2H), 4.10 (s, 3H).

Workup

  1. customthe precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-9ebc4101ca4f421a889db1cfaf7674c0
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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