2,2,2-Trifluoroethanol → HCID 178448491, compound

HRID 538793Notes

Reaction equation

HRID 538793 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:20])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2F)/[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:25]([OH:30])[C:26]([F:29])([F:28])[F:27].CC([O-])(C)C.[K+]>C1COCC1.O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:20])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:30][CH2:25][C:26]([F:29])([F:28])[F:27])/[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 23665647Potassium tert-butoxideHCID 178448489HCID 178448489, compound

Product 1

HCID 178448491HCID 178448491, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Example 75A (537 mg, 1.45 mmol), trifluoroethanol (87 μL, 2.18 mmol) and potassium 2-methylpropan-2-olate (2.18 mL, 2.18 mmol) in THF (10 mL) was stirred at room temperature for 3 hrs. The mixture was diluted with water and extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 258 mg (40%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 0.99 (t, J=7.32 Hz, 3H) 1.36 (s, 9H) 1.40 (dd, J=7.63 Hz, 2H) 1.82 (m, 2H) 4.19 (t, J=7.32 Hz, 2H) 4.48 (q, J=8.54 Hz, 2H) 6.65 (s, 1H) 7.02 (d, J=8.54 Hz, 1H) 8.03 (d, J=2.75 Hz, 1H). MS (DCI/NH4+) m/z 449 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fdf58222b09b4d9cb46df1460225538b
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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