Iodoethane → HCID 67383776, compound

HRID 245213Notes

Reaction equation

HRID 245213 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:6]([CH3:23])=[C:5]2[C:24]([O:26][CH3:27])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:35][CH3:36]>CN(C)C=O.[NH4+].[Cl-]>[CH2:35]([O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([C:24]([O:26][CH3:27])=[O:25])=[C:6]([CH3:23])[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[N:8]2)=[CH:3][C:2]=1[F:1])[CH3:36]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 136338336HCID 136338336, compound

Product 1

HCID 67383776HCID 67383776, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a mixture of methyl 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.35 g, 24.64 mmol) and Cs2CO3 (24.08 g, 73.9 mmol) in N,N-dimethylformamide (100 mL) at room temperature was added iodoethane (3.98 mL, 49.3 mmol) slowly. The mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous NH4Cl and extracted with methylene chloride. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride) to afford methyl 7-(ethyloxy)-6-fluoro-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (9.35 g, 93% yield). 1H NMR (400 MHz, DMSO-d6) 67.93-7.99 (m, 2H), 7.88 (d, J=7.78 Hz, 1H), 7.76 (t, J=7.65 Hz, 1H), 7.69 (d, J=8.53 Hz, 1H), 7.63 (d, J=12.30 Hz, 1H), 4.30 (q, J=7.03 Hz, 2H), 4.06 (s, 3H), 2.33 (s, 3H), 1.44 (t, J=6.90 Hz, 3H); MS (m/z) 408.1 (M+H+).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via column chromatography (ISCO, 120 g silica, 0-20% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-3ba20c3b1bd848e8a2ec63f595055c49
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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