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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 68340Generated: October 26, 2026

Sodium Carbonate → 3-(2-tert-butoxy-6-phenylpyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

https://huagongshe.com/reaction/68340

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantPhenylboronic AcidHCID 66827—
ReactantDimethoxyethane ethanol waterHCID 86587095—
Reactant3-(2-tert-butoxy-6-chloropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridineHCID 87402305—
CatalystHCID 178418476HCID 178418476—
SolventEthyl AcetateHCID 8857—
Product3-(2-tert-butoxy-6-phenylpyridin-4-yl)-1H-pyrrolo[2,3-b]pyridineHCID 67442398—

Reaction Conditions

Temperature160 °C

Reaction Steps

To a solution of EXAMPLE 34C (0.13 g, 0.43 mmol) in 7:3:2 dimethoxyethane/ethanol/water (3 mL) was added phenyl boronic acid (0.053 g, 0.43 mmol), 1M aqueous sodium carbonate (0.6 mL) and dichlorobis (triphenylphosphine)-palladium (II) (0.015 g, 0.022 mmol). The solution was heated to 160° C. in a CEM microwave @100 W for 20 minutes. The crude material was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (Analogix 280, gradient elution, 5-75% ethyl acetate/hexane) gave the title compound. MS (ESI) m/e 344.0 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822446B2
Source datasetuspto-grants-2014_09
ORD IDord-1ba44848956d444286b05d8a93b2232f
Source noteuspto-grants-2014_09