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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81872Generated: October 25, 2026

4-Cyanophenylboronic acid → Benzyl 2-(Benzyloxy)-4-(N-((4'-Cyanobiphenyl-4-Yl)Methyl)-2-(N,4-Dimethylphenyl-Sulfon-Amido)Acetamido)Benzoate

https://huagongshe.com/reaction/81872

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Cyanophenylboronic acidHCID 2734326—
ReactantBenzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateHCID 66728422—
ProductBenzyl 2-(Benzyloxy)-4-(N-((4'-Cyanobiphenyl-4-Yl)Methyl)-2-(N,4-Dimethylphenyl-Sulfon-Amido)Acetamido)BenzoateHCID 86694678—

Reaction Steps

Aryl halide 9 was coupled to 4-cyanophenylboronic acid to give 33 on a 0.1 mmol scale via General Procedure H (73 mg, 71%): δH (400 MHz, CDCl3) 2.39 (s, 3H, CH3), 2.82 (s, 3H, CH3), 3.68 (s, 2H, CH2), 4.85 (s, 2H, CH2), 5.05 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.67 (s, 1H, CH), 6.69 (d, J=1.2 Hz, 1H, CH), 7.22-7.34 (m, 13H, CH), 7.38-7.40 (m, 2H, CH), 7.61 (d, J=8.0 Hz, 2H, CH), 7.64 (d, J=8.4 Hz, 2H, CH), 7.70-7.72 (m, 3H, CH), 7.84 (d, J=8.4 Hz, 1H, CH); δC (100 MHz, CDCl3) 21.4, 36.0, 51.4, 52.7, 67.0, 70.7, 111.0, 114.0, 118.7, 119.9, 120.8, 126.9, 127.3, 127.4, 127.5, 128.0, 128.2, 128.2, 128.5, 128.5, 128.7, 129.5, 130.8, 132.4, 132.5, 133.1, 135.6, 135.7, 137.1, 138.4, 143.3, 144.8, 158.8, 165.2, 167.1, 167.6; LRMS (ES+) calcd for [C45H39N3O6S+H] 750.26 found 750.26.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846707B2
Source datasetuspto-grants-2014_09
ORD IDord-4cbf91b33b21489fbd59ece0cd03da13
Source noteuspto-grants-2014_09