α,α-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetonitrile → HCID 67450365, compound

HRID 1853772Notes

Reaction equation

HRID 1853772 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:17]=[CH:16][S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[CH3:18][C:19]([C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=1)([CH3:22])[C:20]#[N:21]>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:14])[C:5]3[S:15][CH:16]=[CH:17][C:4]=3[C:3]=2[C:2]=1[C:26]1[CH:27]=[CH:28][C:23]([C:19]([CH3:22])([CH3:18])[C:20]#[N:21])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 59322050α,α-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetonitrileHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67450365HCID 67450365, compoundYield 57.9%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (380 mg, 1.2 mmol) was reacted with 2-methyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (500 mg, 1.9 mmol) to afford the desired product (260 mg, 56%) as a brown solid: ESI MS m/z 375 [C22H18N2O2S+H]+.

Sources & evidence

ORD record
ord-67dd895114194392a51f066e9bd8556a
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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