4-(2-Cyanoprop-2-yl)benzeneboronic acid → 2-{4-[5-Amino-6-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-pyrazin-2-yl]-phenyl}-2-methyl-propionitrile

HRID 2091591Notes

Reaction equation

HRID 2091591 reaction equation
[C:1]([C:3]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2].[NH2:15][C:16]1[C:17]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[C:29](=[O:33])[NH:28][CH2:27][CH2:26]3)=[N:18][C:19](Br)=[CH:20][N:21]=1>C(O)CCC>[NH2:15][C:16]1[N:21]=[CH:20][C:19]([C:9]2[CH:10]=[CH:11][C:6]([C:3]([CH3:5])([CH3:4])[C:1]#[N:2])=[CH:7][CH:8]=2)=[N:18][C:17]=1[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[NH:28][CH2:27][CH2:26]2

Participants

4

Reactant 2

HCID 441193244-(2-Cyanoprop-2-yl)benzeneboronic acidHCID 866702106-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 706544952-{4-[5-Amino-6-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-pyrazin-2-yl]-phenyl}-2-methyl-propionitrileYield 82%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

General method B was applied to 4-(2-cyanopropan-2-yl)phenylboronic acid (79 mg, 0.42 mmol) and 6-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (150 mg, 0.38 mmol) in n-butanol (2 mL) to give 2-{4-[5-amino-6-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-pyrazin-2-yl]-phenyl}-2-methyl-propionitrile (119 mg, 82% yield) after purification by column chromatography on silica (2-5% MeOH/DCM eluent).

Sources & evidence

ORD record
ord-0ca26c8d7f174442b54b54652bab7d40
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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