(R)-2-(1-bromopropan-2-yl)isoindoline-1,3-dione → (R)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

HRID 872467Notes

Reaction equation

HRID 872467 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[CH2:16][C@H:17]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])[CH3:18]>>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[C@H:17]([CH3:18])[CH2:16][N:12]1[CH:13]=[CH:14][C:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[CH:9]=2)=[N:11]1

Participants

3

Reactant 2

HCID 2733602(R)-2-(1-bromopropan-2-yl)isoindoline-1,3-dioneHCID 178422844HCID 178422844, compound

Product 1

HCID 70657415(R)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-methylbenzonitrileYield 17%

Procedure

2-Methyl-4-(1H-pyrazol-3-yl)benzonitrile (2.23 g, 12.2 mmol) was reacted with (R)-2-(1-bromopropan-2-yl)isoindoline-1,3-dione (3.92 g, 14.6 mmol) using the method of Example 27(a). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane) to yield 0.753 g (17%) of the title compound. Product was used in the next step without analysis.

Workup

  1. customCrude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-b38ab458021045cbafd7a6e0be5ca5f6
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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