Cesium carbonate → HCID 68961424, compound

HRID 269384Notes

Reaction equation

HRID 269384 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=[C:13]2[OH:24].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:32][C:33]#[N:34]>CC(C)=O.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([F:22])([F:21])[F:23])[CH:14]=[C:13]2[O:24][CH2:32][C:33]#[N:34]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 178516131HCID 178516131, compound

Product 1

HCID 68961424HCID 68961424, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-(1-benzofuran-2-yl)-4-hydroxy-2-(trifluoromethyl)quinoline (0.770 g, 2.34 mmol) in acetone (40 mL) at room temperature was added Cs2CO3 (0.839 g, 2.57 mmol) followed by bromoacetonitrile (0.326 mL, 4.68 mmol) dropwise. The reaction was stirred at this temperature for 18 hours and then diluted with EtOAc (200 mL). The organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was recrystallized from EtOAc:Hexane to afford the product (0.711 g, 82%) as a off-white solid, mp 174-176° C. Mass spectrum (+APCI, [M+H]+) m/z 369. 1H NMR (500 MHz, DMSO-d6): δ 8.61 (d, 1H, J=2.0), 8.48 (dd, 1H, J=2.0, 8.8 Hz), 8.23 (d, 1H, J=8.8 Hz), 7.78 (s, 1H), 7.70-7.75 (m, 2H), 7.67 (s, 1H), 7.39 (t, 1H, J=7.2 Hz,), 7.30 (t, 1H, J=7.6 Hz), and 5.70 ppm (s, 2H), Elemental analysis for C20H11F3N2O2: Calculated: C, 65.22; H, 3.01; N, 7.61. Found: C, 65.02; H, 2.87; N, 7.51.

Workup

  1. washThe organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-378676a80d664c63a92ee1504000e03e
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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