Isopropyl iodide → 5-Benzyloxy-6-bromo-2-isopropoxy-4-(trifluoromethyl)quinoline

HRID 1350136Notes

Reaction equation

HRID 1350136 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([Br:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([C:21]([F:24])([F:23])[F:22])=[CH:12][C:13](=[O:20])[NH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].[CH:27](I)([CH3:29])[CH3:28]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]([Br:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([C:21]([F:24])([F:22])[F:23])=[CH:12][C:13]([O:20][CH:27]([CH3:29])[CH3:28])=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 25953Cesium fluorideHCID 210943815-benzyloxy-6-bromo-4-(trifluoromethyl)-1H-quinolin-2-one

Product 1

HCID 210943805-Benzyloxy-6-bromo-2-isopropoxy-4-(trifluoromethyl)quinolineYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-benzyloxy-6-bromo-4-(trifluoromethyl)-1H-quinolin-2-one (11.7 g, 29.4 mmol) and CsF (17.8 g, 117 mmol) in 150 mL DMF was added isopropyl iodide (19.9 g, 117 mmol). After 28 h, the mixture was partitioned between EtOAc (500 mL) and water (250 mL) and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (200 mL), brine (100 mL), dried over MgSO4, filtered and concentrated to afford 13 g (100%) of 5-benzyloxy-6-bromo-2-isopropoxy-4-(trifluoromethyl)quinoline. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 1H, J=9.0), 7.55–7.65 (m, 3H), 7.38–7.48 (m, 2H), 7.32–7.38 (m, 1H), 7.31 (s, 1H), 5.54 (sept, 1H, J=6.2), 5.06 (s, 2H), 1.42 (d, 6H, J=6.2).

Workup

  1. customthe mixture was partitioned between EtOAc (500 mL) and water (250 mL)
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water (200 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f116e0eed9ae416ba585d7e4c0a13066
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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