2,4-Dichloropyridine → HCID 86685258, compound

HRID 522921Notes

Reaction equation

HRID 522921 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:22][C:23]1[CH:28]=[C:27](Cl)[CH:26]=[CH:25][N:24]=1>C(O)(C)C>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:9]2[CH2:8][CH:7]([O:6][C:5]3[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:10]2)[N:24]=1

Participants

5

Reactant 3

HCID 335152,4-DichloropyridineHCID 81531DiisopropylethylamineHCID 214287303-(4-Fluorophenoxy)azetidine

Product 1

HCID 86685258HCID 86685258, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(4-fluorophenoxy)azetidine (557 mg, 3.37 mmol) [prepared as described in Example AAA] in isopropanol (10 mL, 3 mL/mmol) was added DIPEA (1.5 mL, 8.42 mmol) and 2,4-dichloropyridine (500 mg, 3.37 mmol) and the mixture was heated at 80° C. for 7 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×20 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 2-chloro-6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine (500 mg, 55%) as a solid. Observed mass (M+1): 279.1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-f49ab99dbfd64fcc97f5ca075ebcd438
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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