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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1947409Generated: October 31, 2026

4-Cyanophenylboronic acid → 5-{4'-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1'-biphenyl-4-yl}pyridine-2-carbonitrile

https://huagongshe.com/reaction/1947409

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Cyanophenylboronic acidHCID 2734326—
Reactant2-Cyanopyridine-5-boronic acid pinacol esterHCID 16414188—
Reactant(3aR,6aR)-1-(4-Bromophenyl)-5-methyloctahydropyrrolo[3,4-b]pyrroleHCID 44221503—
Product5-{4'-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]-1,1'-biphenyl-4-yl}pyridine-2-carbonitrileHCID 24743817—

Reaction Steps

The title compound was prepared according to the procedure described in Example 7D, substituting the product of Example 41A for the product of Example 7C and substituting 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile for 4-cyanophenylboronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 8.99 (d, J=2.14 Hz, 1H) 8.03 (dd, J=8.09, 2.29 Hz, 1H) 7.76 (d, J=7.93 Hz, 1H) 7.68-7.73 (m, 2H) 7.59-7.67 (m, 2H) 7.52-7.58 (m, 2H) 6.67 (d, J=8.85 Hz, 2H) 4.12-4.23 (m, 3.05 Hz, 1H) 3.53-3.62 (m, 1H) 3.26-3.35 (m, 1H) 2.92-3.03 (m, 1H) 2.69-2.78 (m, 1H) 2.48-2.67 (m, 3H) 2.33 (s, 3H) 2.13-2.25 (m, 1H) 1.91-2.03 (m, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08399468B2
Source datasetuspto-grants-2013_03
ORD IDord-ba6cbbd90ada4b408cd569abcdf6f95c
Source noteuspto-grants-2013_03