9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 67447379, compound

HRID 1853720Notes

Reaction equation

HRID 1853720 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].CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:35])[C:33]#[N:34])=[CH:28][CH:27]=2)O1>>[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:31]=[CH:30][C:29]([CH:32]([CH3:35])[C:33]#[N:34])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 67452172HCID 67452172, compound

Product 1

HCID 67447379HCID 67447379, compoundYield 83.1%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (1.5 g, 4.84 mmol) was reacted with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile (1.87 g, 7.26 mmol) to afford the desired product (1.45 g, 82%) as a brown solid: ESI MS m/z 361 [C21H16N2O2S+H]+.

Sources & evidence

ORD record
ord-092bc4d5c8754d259aefa63d3f9885ac
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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