4-Fluoroiodobenzene → HCID 117849013, compound

HRID 1477662Notes

Reaction equation

HRID 1477662 reaction equation
Cl.[CH2:2]1[C:4]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6][NH:5]2)[CH2:3]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.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:17][C:18]1[CH:23]=[CH:22][C:21]([N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:4]32[CH2:3][CH2:2]3)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 23676156Sodium t-butoxideHCID 86346447tert-Butyl 4,7-diazaspiro[2.5]octane-7-carboxylate hydrochloride

Product 1

HCID 117849013HCID 117849013, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a toluene solution (2.0 mL) of tert-butyl 4,7-diazaspiro[2.5]octane-7-carboxylate hydrochloride (100 mg, 0.402 mmol), 1-fluoro-4-iodobenzene (446 mg, 2.01 mmol), sodium tert-butoxide (77.3 mg, 0.804 mmol), and bis(tri-tert-butylphosphine)palladium (0) (41.1 mg, 0.0804 mmol) were added and the resultant mixture was stirred at 110° C. for 1 hour and 30 minutes. After completion of the reaction, the reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1) to obtain the title compound (116 mg, yield 94%).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1)

Sources & evidence

ORD record
ord-8f6643e0194341d29d677f3387d2b31d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…