4-(4-Bromophenyl)-N-(3-cyano-4-(isopropylsulfonyl)phenyl)butanamide → N-(3-Cyano-4-(isopropylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamide

HRID 735509Notes

Reaction equation

HRID 735509 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][B:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)[O:4][CH2:3]1.BrC1C=CC(CCCC([NH:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])=[C:36]([C:46]#[N:47])[CH:35]=2)=O)=CC=1>>[C:46]([C:36]1[CH:35]=[C:34]([NH:33][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([B:5]3[O:4][CH2:3][C:2]([CH3:1])([CH3:20])[CH2:7][O:6]3)=[CH:13][CH:12]=2)[CH:39]=[CH:38][C:37]=1[S:40]([CH:43]([CH3:44])[CH3:45])(=[O:42])=[O:41])#[N:47]

Participants

3

Reactant 2

HCID 578427724-(4-Bromophenyl)-N-(3-cyano-4-(isopropylsulfonyl)phenyl)butanamideHCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid

Product 1

HCID 57842872N-(3-Cyano-4-(isopropylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamideYield 97%

Procedure

Using a procedure analogous to that used to prepare 2A, 9C (600 mg, 1.34 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 9D (625 mg, 97%) as a brown foam. MS (ESI) m/z 413.1 (M−H)− for free boronic acid.

Sources & evidence

ORD record
ord-66319b2f7bdb4a5287437cd0c8cdbd2b
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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