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Cesium carbonate → 4-Fluoro-1-(3-nitro-5-(trifluoromethyl)phenyl)piperidine

HRID 2200144
Notes
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Reaction equation

HRID 2200144 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.Cl.[F:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:16][CH:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[CH2:19][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 27591584-Fluoropiperidine hydrochlorideHCID 70154111-Bromo-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 900206124-Fluoro-1-(3-nitro-5-(trifluoromethyl)phenyl)piperidineYield 63.4%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Mix 1-bromo-3-nitro-5-(trifluoromethyl)benzene (700 mg, 2.59 mmol), 4-fluoropiperidine hydrochloride (544 mg, 3.89 mmol), cesium carbonate (2.5 g, 7.77 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 48 mg, 0.077 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 47 mg, 0.052 mmol] in dioxane (10 mL), Stir the mixture under nitrogen atmosphere at 100° C. for 16 hrs. Cool the reaction mixture to room temperature, dilute it with water (10 mL), extract with ethyl acetate (10 mL×2), combine the organic layers, wash with brine (15 mL) and dry over anhydrous sodium sulfate. Concentrate the filtrate to get the crude product. Purify by flash chromatography (silica gel, 100% PE) to yield the target compound (480 mg, 63%).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. extractionextract with ethyl acetate (10 mL×2)
  3. washwash with brine (15 mL)
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationConcentrate the filtrate
  6. customto get the crude product
  7. customPurify by flash chromatography (silica gel, 100% PE)

Sources & evidence

ORD record
ord-ad5bb0cf52584ba09693fc092e428a39
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359338B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes