1-Bromo-4-fluorobenzene → HCID 117848941, compound

HRID 1477583Notes

Reaction equation

HRID 1477583 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.Br[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>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(C)C=CC=CC=1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 117848941HCID 117848941, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a toluene solution (4 mL) of tert-butyl (R)-piperidin-3-yl-carbamate (500 mg, 2.50 mmol), 4-bromo-1-fluorobenzene (0.250 mL, 2.28 mmol), 2-(di-tert-butylphosphino)biphenyl (136 mg, 0.500 mmol), tris(dibenzylideneacetone)dipalladium (0) (104 mg, 0.130 mmol), and sodium tert-butoxide (307 mg, 3.50 mmol) was stirred at 100° C. for 4 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (hexane/ethyl acetate=100/0→70/30 (v/v)) to obtain the title compound (550 mg, yield 82%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. custompurified by silica gel column chromatography (hexane/ethyl acetate=100/0→70/30 (v/v))

Sources & evidence

ORD record
ord-b042304be401451db65f81fa95cc6181
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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