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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1623956Generated: November 2, 2026

Sodium methanesulfinate → (1aR,5aR)-2-(4-(methylsulfonyl)pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid

https://huagongshe.com/reaction/1623956

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium methanesulfinateHCID 2733271—
Reactant(1aR,5aR)-2-(4-bromopyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acidHCID 68182432—
SolventDimethyl SulfoxideHCID 679—
SolventWaterHCID 962—
Product(1aR,5aR)-2-(4-(methylsulfonyl)pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic AcidHCID 6818238962.6%

Reaction Steps

A solution of (1aR,5aR)-2-(4-bromopyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (80 mg, 0.25 mmol) and sodium methanesulfinate (28 mg, 0.28 mmol) in DMSO (1.5 mL) was stirred overnight at 80° C. The reaction was diluted with H2O, and then extracted with DCM (3×). The combined organics were washed with H2O, dried, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (50 mg). LCMS m/z=320.2 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778950B2
Source datasetuspto-grants-2014_07
ORD IDord-d0a281983f1947feb3e36ecc634b2248
Source noteuspto-grants-2014_07