Imidazole → HCID 67409251, compound

HRID 1897437Notes

Reaction equation

HRID 1897437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][OH:14])[N:6]=[CH:5]2.N1C=CN=C1.[Si:20](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[N:6]=[CH:5]2

Participants

6

Reactant 3

HCID 795Imidazole2×HCID 94078tert-Butyldiphenylchlorosilane2×HCID 57418748HCID 57418748, compound

Product 1

HCID 67409251HCID 67409251, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Crude 3-(5-Bromoindazol-1-yl)-propan-1-ol (2s) (2.1 mmol) and imidazole (0.22 g, 3.2 mmol) were dissolved in 10 mL CH2Cl2. tert-Butyldiphenylsilyl chloride (0.58 g, 2.1 mmol) was added to the solution and the reaction was stirred at room temperature for 4 hours. Additional amounts of imidazole (0.07 g, 1.0 mmol) and tert-butyldiphenylsilyl chloride (0.16 g, 0.63 mmol) were added and the reaction was stirred at room temperature overnight. The mixture was diluted with Et2O and washed sequentially with an aqueous 3% HCl solution and brine. The aqueous phases were extracted once with Et2O. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel with 1:6 Et2O/hexane to afford (3s) (1.0 g, 96% over two steps) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.92 (s, 1H), 7.86 (s, 1H), 7.61 (d, J=7.8 Hz, 4H), 7.44-7.42 (m, 3H), 7.36-7.33 (m, 5H), 4.53 (t, J=10.2 Hz, 2H), 3.63 (t, J=9.0 Hz, 2H), 2.16-10 (m, 2H), 1.08 (s, 9H); HPLC (5 to 95%) 4.72 min.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. washwashed sequentially with an aqueous 3% HCl solution and brine
  3. extractionThe aqueous phases were extracted once with Et2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified on silica gel with 1:6 Et2O/hexane

Sources & evidence

ORD record
ord-06fea7194dfc4ab1a034676af0842c40
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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