2,2,2-Trifluoroethanol → HCID 67979519, compound

HRID 539298Notes

Reaction equation

HRID 539298 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].CS(O[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=1)(=O)=O>C1COCC1.CN(C=O)C>[Br:21][C:19]1[CH:18]=[N:17][CH:16]=[C:15]([CH2:14][O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:20]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 57885697HCID 57885697, compound

Product 1

HCID 67979519HCID 67979519, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2,2-Trifluoroethanol (0.434 g, 4.34 mmol) was added to a suspension of NaH (0.198 g, 4.96 mmol) in THF (10 mL). When gas evolution had ceased, a solution of (5-bromopyridin-3-yl)methyl methanesulfonate (see WO2007/076247; 1.10 g, 4.13 mmol) in DMF was added. The resulting mixture was stirred for 2 h at r.t. and then the volatile solvent was evaporated. The remaining solution was diluted with water and extracted with EtOAc (3×30 mL). The combined extracts were dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica using gradient elution with EtOAc in heptane to give 227 mg of the title compound (20% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.92 (q, 2 H), 4.70 (s, 2 H), 7.87 (m, 1 H), 8.50 (m, 1 H), 8.66 (d, 1 H); MS (EI) m/z 269 M+.

Workup

  1. customthe volatile solvent was evaporated
  2. additionThe remaining solution was diluted with water
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica using gradient elution with EtOAc in heptane

Sources & evidence

ORD record
ord-a00e3b7532074c13964022202bca5a74
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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