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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1772151Generated: October 30, 2026

Bis(pinacolato)diborane → 2-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl Acetate

https://huagongshe.com/reaction/1772151

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBis(pinacolato)diboraneHCID 2733548—
Reactant2-Bromo-6-(5-(dimethylamino)-1-oxoisoindolin-2-yl)benzyl AcetateHCID 66610297—
Reactant2-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-thieno[3,2-c]pyrrol-6(5H)-oneHCID 89824183—
Product2-(5-(Dimethylamino)-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl AcetateHCID 86699872100%

Reaction Steps

Using the same general procedure as described for the preparation of 102g reaction of 123d (2.65 g, 6.59 mmol) with bis(pinacolato)diboron (5.02 g, 19.8 mmol) gave a 100% yield (3.00 g) of 123e as a brown solid: mp 75-76° C.; 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 1H, J=4.2, 1.8 Hz), 7.76 (d, 1H, J=8.7 Hz), 7.45 (m, 2H), 6.80 (dd, 1H, J=8.7, 2.1 Hz), 6.69 (s, 1H), 5.13 (s, 2H), 4.69 (s, 2H), 3.08 (s, 6H), 1.93 (s, 3H), 1.34 (s, 12H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09249123B2
Source datasetuspto-grants-2016_02
ORD IDord-314f124837b74401b5ffd643a401f4fa
Source noteuspto-grants-2016_02