Imidazole → HCID 68492781, compound

HRID 1944211Notes

Reaction equation

HRID 1944211 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:15])([CH3:14])[NH:9][CH:10]2[CH3:13])=[CH:5][C:4]=1[OH:16].[CH3:17][CH:18]([Si:20](Cl)([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH3:19].N1C=CN=C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:15])([CH3:14])[NH:9][CH:10]2[CH3:13])=[CH:5][C:4]=1[O:16][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 68490283HCID 68490283, compound

Product 1

HCID 68492781HCID 68492781, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

239 (183 mg, 0.83 mmol), TIPS-Cl (237 mg, 3.5 mmol) and imidazole (237 mg, 3.5 mmol) in DCM (10 ml) were stirred at rt for 24 h. The reaction mixture was quenched with water (5 ml) and extracted with DCM (3×10 ml). The combined organic extracts were washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. Purification (personal flashmaster: 20 g, EtOAc:MeOH:TEA; 100:10:1) afforded the title compound (332 mg) as a yellow oily solid. 1H NMR (270 MHz; CDCl3) 1.07 (18H, d, J=6.4 Hz, 6×CH3CH), 1.08 (3H, s, CH3), 1.15-1.28 (3H, m, 3×CHCH3), 1.25 (3H, s, CH3), 1.21 (3H, d, J=6.4 Hz, CH3CH), 2.44 (1H, d, J=15.8 Hz, CHH), 2.65 (1H, d, J=15.8 Hz, CHH), 3.74 (3H, s, OCH3), 4.0 (1H, q, J=6.4 Hz, CHCH3), 6.46 (1H, s, CH), 6.67 (1H, s, CH). LC/MS (ES+) tr=1.8 min, m/z 378.24 (M++H).

Workup

  1. customThe reaction mixture was quenched with water (5 ml)
  2. extractionextracted with DCM (3×10 ml)
  3. washThe combined organic extracts were washed with brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification (personal flashmaster: 20 g, EtOAc:MeOH:TEA; 100:10:1)

Sources & evidence

ORD record
ord-f23126eed3534dd5ba59575fc3b070d0
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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