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

HRID 872462Notes

Reaction equation

HRID 872462 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 5702573(S)-2-(1-bromopropan-2-yl)isoindoline-1,3-dioneHCID 178422844HCID 178422844, compound

Product 1

HCID 70657327(S)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-methylbenzonitrileYield 25.4%

Procedure

2-Methyl-4-(1H-pyrazol-3-yl)benzonitrile (2.35 g, 12.2 mmol) was reacted with (S)-2-(1-bromopropan-2-yl)isoindoline-1,3-dione (3.61 g, 13.5 mmol) using the method of Example 27(a). Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane) to yield 1.15 g (25%) of the title compound. 1H-NMR (400 MHz; CDCl3): δ 1.59 (d, 3H), 2.47 (s, 3H), 4.41 (m, 1H), 4.83 (m, 2H), 6.46 (d, 1H), 7.39 (m, 2H), 7.47 (m, 2H), 7.69 (m, 2H), 7.78 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-b87b1f404af248aba9b76af0ff232596
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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