Pyridine, 2,4,6-trichloro- → HCID 117678380, compound

HRID 1778186Notes

Reaction equation

HRID 1778186 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]1([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

5

Reactant 3

HCID 27665Pyridine, 2,4,6-trichloro-HCID 78148CyanocyclobutaneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 117678380HCID 117678380, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2,4,6-trichloropyridine (1.00 g, 5.48 mmol) and cyclobutanecarbonitrile (0.53 mL, 5.5 mmol) in anhydrous THF (27 mL) at −78° C. and under nitrogen was added lithium bis(trimethylsilyl)amide (6.0 mL, 6.0 mmol, 1.0 M solution in THF). The cooling bath was removed and stirring continued for 1 h. The reaction was quenched by the addition of sat. aq. NH4Cl, extracted with CH2Cl2 and organics dried over MgSO4. Following concentration, the reaction residue was purified by flash column chromatography (100:0 heptanes/EtOAc 85:15 heptanes/EtOAc) to afford the title compound as a white solid (0.995 g, 76%); 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 2H), 2.92-2.80 (m, 2H), 2.68-2.40 (m, 3H), 2.23-2.08 (m, 1H).

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched by the addition of sat. aq. NH4Cl
  3. extractionextracted with CH2Cl2
  4. dry with materialorganics dried over MgSO4
  5. concentrationconcentration
  6. customthe reaction residue was purified by flash column chromatography (100:0 heptanes/EtOAc 85:15 heptanes/EtOAc)

Sources & evidence

ORD record
ord-2711a186652342fbbe2855b4c15eab1d
Source dataset
uspto-grants-2016_02
Patent number
US09266862B2

Reaction notes

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