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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 530447Generated: November 2, 2026

Sodium Carbonate → 2-(6-Chloropyridin-2-yl)-1-methyl-1H-indole

https://huagongshe.com/reaction/530447

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant2-Chloro-6-iodopyridineHCID 18931860—
Reactant(1-Methyl-1H-indol-2-yl)boronic acidHCID 22733820—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Product2-(6-Chloropyridin-2-yl)-1-methyl-1H-indoleHCID 86700704100.2%

Reaction Steps

2-Chloro-6-iodopyridine (400 mg, 1.67 mmol), N-methylindole-2-boronic acid (292 mg, 1.67 mmol), tetrakis(triphenylphosphine)palladium (0) (154 mg, 0.13 mmol) and Na2CO3 (442 mg, 4.18 mmol) were dissolved in water (10 mL) and dioxane (10 mL) and heated using a microwave (110° C., absorption high) for 1 h. The solvents were removed in vacuo and the residue was partitioned between DCM (50 mL) and water (30 mL). The aq fraction was extracted with DCM (30 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound (406 mg) as a brown gum. LCMS (ES+): 243.2 [MH]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353086B2
Source datasetuspto-grants-2016_05
ORD IDord-548650d19e1f4a4f8b1a473ecfd73a68
Source noteuspto-grants-2016_05