Diisopropylamine → HCID 57690820, compound

HRID 401496Notes

Reaction equation

HRID 401496 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[C:20]([N:39]1[CH:43]=[C:42]([CH:44]=[O:45])[N:41]=[CH:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([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>O1CCCC1>[F:13][C:14]1[C:19]([CH:44]([C:42]2[N:41]=[CH:40][N:39]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:43]=2)[OH:45])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 97462-FluoropyridineHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 57690820HCID 57690820, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A 2.5M n-butyl lithium in hexanes solution (6 ml, 15 mmol) was added dropwise to a solution of diisopropylamine (2.12 ml, 15 mmol) in tetrahydrofuran (30 ml), cooled to −78° C. The reaction mixture was allowed to warm up to 0° C. for 30 minutes before being cooled down to −78° C. 2-Fluoropyridine (1.36 g, 14 mmol) in tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was stirred at −78° C. for 1 hour. A solution of 1-trityl-1H-imidazole-4-carbaldehyde (4.5 g, 13.3 mmol) in tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was allowed to warm up to room temperature and was stirred for 18 hours. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate and extracted into ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound (1.3 g, 22% yield).

Workup

  1. temperatureto warm up to 0° C. for 30 minutes
  2. temperaturebefore being cooled down to −78° C
  3. temperatureto warm up to room temperature
  4. stirringwas stirred for 18 hours
  5. customThe reaction was quenched with a saturated aqueous solution of sodium bicarbonate
  6. extractionextracted into ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-d9a45a5c2cac47f9a4198bbc616e27fd
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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