Triethylamine → 6-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Chloromethyl 2-(trimethylsilyl)ethyl ether	HCID 2724271	—
Reactant	6-Chloro-5-iodo-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine	HCID 89558234	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine	HCID 123502316	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

6-Chloro-5-iodo-2-(methylsulfonyl)-1H-imidazo[4,5-b]pyridine (for preparation see WO 2012116145; 1.5 g) and triethylamine (875 μL) are dissolved in tetrahydrofurane (12 mL), cooled to 0° C. and treated with (2-(chloromethoxy)ethyl)trimethylsilane (SEM-Cl; 890 μL). The mixture is stirred for 30 minutes while warming to room temperature. Then the mixture is partitioned between saturated aqueous NH4Cl and ethylacetate. The organic phase is washed with water and brine. After drying (MgSO4) the solvents are evaporated in vacuo to give the title compound. LC (method 1): tR=1.22 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09187477B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-a7b0eeead3d24fa883a10694a7c67d27
Source note	uspto-grants-2015_11