Pyridine, 2,4,6-trichloro- → HCID 59617901, compound

HRID 2386163Notes

Reaction equation

HRID 2386163 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.Cl.[CH:11]1([C:14]2([F:18])[CH2:17][NH:16][CH2:15]2)[CH2:13][CH2:12]1.CCN(C(C)C)C(C)C>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:16]2[CH2:17][C:14]([CH:11]3[CH2:13][CH2:12]3)([F:18])[CH2:15]2)[CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

5

Reactant 3

HCID 27665Pyridine, 2,4,6-trichloro-HCID 81531DiisopropylethylamineHCID 665896423-Cyclopropyl-3-fluoroazetidine hydrochloride

Product 1

HCID 59617901HCID 59617901, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4,6-trichloropyridine (3.0 g, 16.4 mmol), 3-cyclopropyl-3-fluoroazetidine hydrogen chloride (2.49 g, 16.4 mmol) and DIPEA (7.09 ml, 41.0 mmol) in ethanol (40 ml) was heated under reflux for 1 h. Reaction mixture cooled to room temperature then concentrated to dryness in vacuo. Crude product purified by flash chromatography on silica (0 to 100% EtOAc: petrol) to give title compound as a white solid (1.56 g, 36%). 1H NMR (CDCl3) 0.52-0.48 (2H, m), 0.72-0.67 (2H, m), 1.42-1.31 (1H, m), 3.91 (2H, ddd), 4.05 (2H, ddd), 6.20 (2H, s). ES+261.30.

Workup

  1. temperatureunder reflux for 1 h
  2. customReaction mixture
  3. concentrationthen concentrated to dryness in vacuo
  4. customCrude product purified by flash chromatography on silica (0 to 100% EtOAc: petrol)

Sources & evidence

ORD record
ord-f05536e7db884a1ca1f5066112f30fd3
Source dataset
uspto-grants-2012_09
Patent number
US08268811B2

Reaction notes

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