4-(4-Bromophenyl)-N-(4-(tert-butylsulfonyl)-3-cyanophenyl)butanamide → N-(4-(tert-butylsulfonyl)-3-cyanophenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamide

HRID 735514Notes

Reaction equation

HRID 735514 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]([C:43]([CH3:46])([CH3:45])[CH3:44])(=[O:42])=[O:41])=[C:36]([C:47]#[N:48])[CH:35]=2)=O)=CC=1>>[C:43]([S:40]([C:37]1[CH:38]=[CH:39][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:35][C:36]=1[C:47]#[N:48])(=[O:42])=[O:41])([CH3:46])([CH3:44])[CH3:45]

Participants

3

Reactant 2

HCID 578426964-(4-Bromophenyl)-N-(4-(tert-butylsulfonyl)-3-cyanophenyl)butanamideHCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid

Product 1

HCID 57842633N-(4-(tert-butylsulfonyl)-3-cyanophenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)butanamideYield 93%

Procedure

Using a procedure analogous to that used to prepare 2A, 10C (430 mg, 0.930 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 10D (431 mg, 93%) as a brown foam. This crude material was taken on to the next step.

Sources & evidence

ORD record
ord-40fbec6e83354d5c88b6db6c70671822
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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