1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 4-(1-(2-(1,3-Dioxoisomdolin-2-yl)ethyl)-1H-pyrazol-3-yl)-2-methylbenzonitrile

HRID 872460Notes

Reaction equation

HRID 872460 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][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]>>[O:28]=[C:19]1[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:23])[N:18]1[CH2:17][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 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 178422844HCID 178422844, compound

Product 1

HCID 706561574-(1-(2-(1,3-Dioxoisomdolin-2-yl)ethyl)-1H-pyrazol-3-yl)-2-methylbenzonitrileYield 32%

Procedure

2-Methyl-4-(1H-pyrazol-3-yl)benzonitrile (0.949 g, 5.2 mmol) was reacted with N-(2-bromoethyl)phthalimide (1.58 g, 6.2 mmol) using the method of Example 27(a). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane) to yield 0.590 g (32%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.36 (s, 3H), 3.99 (t, 2H), 4.44 (t, 2H), 6.76 (d, 1H), 7.44 (s, 1H), 7.46 (m, 1H), 7.62 (d, 1H), 7.83 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-37588d8c559b45888b30d7b9416845ce
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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