Toluene → 3-[3-(6-Isopropylquinolin-8-yl)-phenyl]-2-[4-(methylsulfonyl)-phenyl]-prop-2-enenitrile

HRID 896689Notes

Reaction equation

HRID 896689 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1)(=[O:14])=[O:13].N1CC[CH2:27][CH2:26][CH2:25]1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH:26]([C:7]1[CH:6]=[C:5]2[C:10](=[C:9]([C:32]3[CH:31]=[C:30]([CH:36]=[C:21]([C:18]4[CH:19]=[CH:20][C:15]([S:12]([CH3:11])(=[O:13])=[O:14])=[CH:16][CH:17]=4)[C:22]#[N:23])[CH:35]=[CH:34][CH:33]=3)[CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)([CH3:27])[CH3:25]

Participants

5

Reactant 4

HCID 1140TolueneHCID 7047QuinolineHCID 8082PiperidineHCID 27609502-(4-(Methylsulfonyl)phenyl)acetonitrile

Product 1

HCID 696943163-[3-(6-Isopropylquinolin-8-yl)-phenyl]-2-[4-(methylsulfonyl)-phenyl]-prop-2-enenitrile

Conditions

Temperature
21 °C

Procedure

A solution of Quinoline 04 (5 g, 18 mmol), 4-methanesulfonylacetonitrile (3.5 g, 18 mmol) from Step 1 and piperidine (0.1 mL) in toluene (5 mL) was heated at 130° C. After 6 h, the mixture was cooled to 21° C. and purified by flash chromatography (eluting with ethylacetate/hexane, 1:1 to 75:25) to afforded the title compound.

Workup

  1. custompurified by flash chromatography (eluting with ethylacetate/hexane, 1:1 to 75:25)

Sources & evidence

ORD record
ord-8451bab0a5a742e684ac51435d4e5a69
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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