2-Cyanopyridine-5-boronic acid pinacol ester → 5-[1-(1,3-Dimethyl-1h-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1h-imidazo[4,5-c]quinolin-8-yl]-pyridine-2-carbonitrile

HRID 445682Notes

Reaction equation

HRID 445682 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1)#[N:25]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:29]5[CH:30]=[CH:31][C:26]([C:24]#[N:25])=[N:27][CH:28]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

3

Reactant 2

HCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 596196685-[1-(1,3-Dimethyl-1h-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1h-imidazo[4,5-c]quinolin-8-yl]-pyridine-2-carbonitrile

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A) and 2-cyanopyridine-5-boronic acid pinacol ester (Frontier Scientific, Logan, USA) to give the title compound as a brown solid. (HPLC: tR 2.42 min (Method A); M+H=396 MS-ES)

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-e7b61ee1921b4b90bd33d71c3a7a09f8
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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