Methanol → 2-Butyl-7-methyl-1H-imidazo[4,5-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	6-Bromo-2-butyl-7-methylimidazo[4,5-b]pyridine	HCID 21464181	—
Reactant	HCID 178418306	HCID 178418306	—
Solvent	Pentane	HCID 8003	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	2-Butyl-7-methyl-1H-imidazo[4,5-b]pyridine	HCID 15015265	87%

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a cooled (-78° C.) stirred solution of 6-bromo-2-butyl-7-methylimidazo[4,5-b]pyridine (98 mg, 0.366 mmol) in THF (4 mL) was added tert-butyllithium (0.86 mL of a 1.7M solution in pentane, 1.46 mmol). After 15 minutes, MeOH (0.5 mL and brine were added the mixture was warmed to room temperature and extracted with EtOAc (4×10 mL). Drying (K2CO3), concentration, and purification (SiO2, 100% EtOAc) gave 60 mg (87%) of the title compound as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05157026
Source dataset	uspto-grants-1992_10
ORD ID	ord-645c74ed2b3f4ecfa85a1ff39f672a31
Source note	uspto-grants-1992_10