Sodium hydride → 3-(4-benzyloxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 2255554Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.[H-].[Na+].[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]=[C:9]2[CH2:11][CH2:12][CH3:13])=[CH:30][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 7-methyl-2-propylimidazo[4,5-b]pyridine (1.00 g, 5.71 mmol) and NaH (189 mg, 1.1 eq) in DMF (25 mL) was stirred for 1 hour and then cooled to 0° C. 4-Benzyloxybenzyl chloride (1.46 g; 1.1 eq) was then added and the ice bath removed. The reaction mixture was stirred for 2.5 hours and was then concentrated in vacuo. The residue was chromatographed on a silica gel flash chromatography column (30×100 mm) eluted with 30% ethyl acetate/hexane to yield 1.07 g (50%) of product.

Workup

customthe ice bath removed
stirringThe reaction mixture was stirred for 2.5 hours
concentrationwas then concentrated in vacuo
customThe residue was chromatographed on a silica gel flash chromatography column (30×100 mm)
washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record: ord-9fe0a88a717147928018dfb0404a5c96
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05240938

Reaction notes

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