Bis(neopentyl glycolato)diboron → N-(3-Cyano-4-(ethylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-methylphenyl)butanamide

HRID 735504Notes

Reaction equation

HRID 735504 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][O:6][B:5](C2C=CC(CCCC(O)=O)=CC=2)[O:4][CH2:3]1.Br[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][C:31]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])=[C:36]([C:45]#[N:46])[CH:35]=2)=[O:32])=[C:24]([CH3:47])[CH:23]=1.CC1(C)COB(B2OCC(C)(C)CO2)OC1>>[C:45]([C:36]1[CH:35]=[C:34]([NH:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][C:25]2[CH:26]=[CH:27][C:22]([B:5]3[O:6][CH2:7][C:2]([CH3:20])([CH3:1])[CH2:3][O:4]3)=[CH:23][C:24]=2[CH3:47])[CH:39]=[CH:38][C:37]=1[S:40]([CH2:43][CH3:44])(=[O:42])=[O:41])#[N:46]

Participants

4

Reactant 3

HCID 2734316Bis(neopentyl glycolato)diboronHCID 578426604-(4-Bromo-2-methylphenyl)-N-(3-cyano-4-(ethylsulfonyl)phenyl)butanamideHCID 578427774-[4-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-butyric acid

Product 1

HCID 57842912N-(3-Cyano-4-(ethylsulfonyl)phenyl)-4-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-methylphenyl)butanamideYield 88%

Procedure

Using a procedure analogous to that used to prepare 2A, 8B (448 mg, 1.00 mmol) was reacted with 5,5,5′,5′-Tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to afford 8C (425 mg, 88%) as an off-white solid. MS (ESI) m/z 413.1 (M−H)− for free boronic acid.

Sources & evidence

ORD record
ord-44e679c837df469fafa7034c812a6dcb
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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