N-bromobutanimide → (S)-(6-(4-bromo-1H-pyrazol-1-yl)-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)(cyclopropyl)methanone

HRID 1051722Notes

Reaction equation

HRID 1051722 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([C:12]([N:14]2[C:23]3[C:18](=[C:19]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:20]([N:24]4[CH:28]=[CH:27][CH:26]=[N:25]4)=[CH:21][CH:22]=3)[CH2:17][CH2:16][C@@H:15]2[CH3:36])=[O:13])[CH2:11][CH2:10]1>CN(C)C=O.O>[Br:1][C:27]1[CH:26]=[N:25][N:24]([C:20]2[C:19]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:14]([C:12]([CH:9]2[CH2:10][CH2:11]2)=[O:13])[C@@H:15]([CH3:36])[CH2:16][CH2:17]3)[CH:28]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118076281(S)-cyclopropyl(2-methyl-5-phenoxy-6-(1H-pyrazol-1-yl)-3,4-dihydroquinolin-1 (2H)-yl)methanone

Product 1

HCID 118076321(S)-(6-(4-bromo-1H-pyrazol-1-yl)-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)(cyclopropyl)methanoneYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (0.025 g, 0.15 mmol) was added to a solution of (S)-cyclopropyl(2-methyl-5-phenoxy-6-(1H-pyrazol-1-yl)-3,4-dihydroquinolin-1 (2H)-yl)methanone (0.050 g, 0.13 mmol) in N,N-dimethylformamide (2 mL), and the resulting solution stirred overnight at room temperature. The reaction mixture was diluted with water (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 1:10, ethyl acetate/petroleum ether) to afford (S)-(6-(4-bromo-1H-pyrazol-1-yl)-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)(cyclopropyl)methanone (0.055 g, 91%) as yellow oil. MS (ESI, pos. ion) m/z 452, 454 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified via preparative thin layer chromatography (eluting with 1:10, ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-9e0b9446a417441e9553b2b7de878944
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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