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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81868Generated: October 25, 2026

3-Cyanophenylboronic acid → benzyl 2-(benzyloxy)-4-(N((3'-cyanobiphenyl-4-yl)methyl)-2-(N,4-dimethylphenyl-sulfon-amido)acetamido)benzoate

https://huagongshe.com/reaction/81868

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Cyanophenylboronic acidHCID 2734325—
ReactantBenzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateHCID 66728422—
Productbenzyl 2-(benzyloxy)-4-(N((3'-cyanobiphenyl-4-yl)methyl)-2-(N,4-dimethylphenyl-sulfon-amido)acetamido)benzoateHCID 68076107—

Reaction Steps

Aryl halide 9 was coupled to 3-cyanophenylboronic acid to give 29 on a 0.1 mmol scale via General Procedure H (58 mg, 60%): δH (400 MHz, CDCl3) 2.33 (s, 3H, CH3), 2.76 (s, 3H, CH3), 3.62 (s, 2H, CH2), 4.78 (s, 2H, CH2), 4.97 (s, 2H, CH2), 5.28 (s, 2H, CH2), 6.60-6.62 (m, 2H, CH), 7.14-7.28 (m, 12H, CH), 7.25-7.28 (m, 2H, CH), 7.38 (d, J=8.0 Hz, 2H, CH), 7.44-7.49 (m, 1H, CH), 7.54-7.57 (m, 3H, CH), 7.71 (dt, J=7.6 and 1.2 Hz, 1H, CH), 7.76 (s, 1H, CH), 7.78 (s, 1H, CH); δC (100 MHz, CDCl3) 21.4, 36.0, 51.4, 52.7, 67.0, 70.7, 112.9, 114.0, 118.6, 120.0, 120.9, 127.0, 127.1, 127.4, 128.0, 128.2, 128.2, 128.5, 128.6, 128.7, 129.5, 129.5, 129.6, 130.5, 130.8, 131.2, 133.1, 135.6, 135.7, 136.8, 138.2, 141.7, 143.3, 158.8, 165.2, 167.1, 167.7; 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-7d0c06e95b564b83a01d73d021189ba2
Source noteuspto-grants-2014_09