Water → HCID 86692457, compound

HRID 1748507Notes

Reaction equation

HRID 1748507 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:23][C:24]1[CH:25]=[CH:26][C:27](F)=[N:28][CH:29]=1.O>O1CCCC1>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:8]2([C:11]#[N:12])[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 27831685-Bromo-2-fluoropyridineHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 86692457HCID 86692457, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After 1,4-dioxaspiro[4,5]decane-8-carbonitrile (2.5 g) was dissolved in tetrahydrofuran (8 ml), 1M tetrahydrofuran-solution of lithium bis(trimethylsilyl)amide (15 ml) was added at 0° C. and stirred for 30 minutes. 5-Bromo-2-fluoropyridine (2.64 g) was further added and stirred at room temperature for two hours. Water was added to the reaction solution, extracted with ethyl acetate and concentrated in vacuo. The residue was purified with silica gel chromatography (n-hexane/ethyl acetate) and the resulting solid was washed with n-hexane to give the titled compound (3.32 g).

Workup

  1. stirringstirred at room temperature for two hours
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified with silica gel chromatography (n-hexane/ethyl acetate)
  5. washthe resulting solid was washed with n-hexane

Sources & evidence

ORD record
ord-0c40b9f34c89422fb2684c4ca45a3b4a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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