4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → 4-(4-(3-Cyanophenylamino)-4-oxobutyl)-3-methylphenylboronic acid

HRID 735640Notes

Reaction equation

HRID 735640 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]([OH:27])[OH:26])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1S(CC)(=O)=O)#[N:2].Br[C:30]1C=CC(CCCC(NC2C=CC=C(C#N)C=2)=O)=C(C)C=1>>[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:28])[CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([B:25]([OH:26])[OH:27])=[CH:23][C:24]=2[CH3:30])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 578426844-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acidHCID 578427454-(4-bromo-2-methylphenyl)-N-(3-cyanophenyl)butanamide

Product 1

HCID 578428184-(4-(3-Cyanophenylamino)-4-oxobutyl)-3-methylphenylboronic acidYield 56%

Procedure

Using a procedure analogous to that used to prepare 6D, 55C (200 mg, 0.56 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 55D (200 mg, 56%) as a solid. MS (ESI) m/z 323.2 (M+H)+.

Sources & evidence

ORD record
ord-7fcfeaecd452406ea14fd159fd828016
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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