Imidazole → HCID 57937420, compound

HRID 1435132Notes

Reaction equation

HRID 1435132 reaction equation
[F:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>C(Cl)Cl>[CH3:20][C:19]([Si:16]([CH3:18])([CH3:17])[O:10][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)[CH3:9])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 57937580960001-33-6

Product 1

HCID 57937420HCID 57937420, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(+/−)-1-(6-Fluoro-2-pyridinyl)ethanol (0.707 g, 5.01 mmol) was dissolved in 50 mL of DCM with stirring, imidazole (0.750 g, 11.0 mmol) and tert-butyldimethylsilyl chloride (0.831 g, 5.51 mmol) were added. The reaction was stirred for 16 h and poured into water. The layers were separated, and the aqueous layer was washed with 1:1 EtOAc/hexanes. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to provide 1.10 g (86%) of the title compound, 1H NMR (400 MHz, DMSO-d6) δ 7.97 (m, 1H), 7.37 (m, 1H), 7.00 (m, 1H), 4.79 (q, J=6.4 Hz, 1H), 1.34 (d, 6.4 Hz, 3H), 0.85 (s, 9H), 0.04 (s, 3H), 0.03 (s, 3H).

Workup

  1. stirringThe reaction was stirred for 16 h
  2. customThe layers were separated
  3. washthe aqueous layer was washed with 1:1 EtOAc/hexanes
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06937df093254af89ccac219b8a708a3
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

Loading…