HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1485603Generated: November 2, 2026
Triethylamine → 6-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine
https://huagongshe.com/reaction/1485603
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 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-CI; 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 |
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| Patent number | US09422312B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-98677b744264430ab08f1419ca1549b4 |
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| Source note | uspto-grants-2016_08 |
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