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Diisopropylethylamine → 2-Chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine

HRID 522892
Notes
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Reaction equation

HRID 522892 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][N:3]=1.Cl.[F:10][C:11]1[CH:21]=[CH:20][C:14]([O:15][CH:16]2[CH2:19][NH:18][CH2:17]2)=[CH:13][CH:12]=1.C(N(C(C)C)C(C)C)C>CC(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:18]2[CH2:19][CH:16]([O:15][C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:21][CH:20]=3)[CH2:17]2)[CH:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27827922-Chloro-4-fluoropyridineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochloride

Product 1

HCID 866852482-Chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridineYield 90.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
84 °C

Procedure

To 2-chloro-4-fluoropyridine (160.0 mg, 1.216 mmol) and 3-(4-fluoro-phenoxy)-azetidine hydrochloride (248 mg, 1.216 mmol) in 2-propanol (3.0 mL) in a disposable sealed tube at RT was added N-ethyl-N-isopropylpropan-2-amine (0.530 mL, 3.04 mmol). The resulting reaction mixture was heated at 84° C. for 18 h, cooled to RT, concentrated, purified using MPLC (5 g cartridge, 12 g column, 0 to 60% EtOAc-hexanes) giving 2-chloro-4-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine (306.1 mg).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-54db301c8e4a49cc980fb99eb3960029
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09334269B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes