1-Fluoro-3-iodobenzene → HCID 61778890, compound

HRID 1049011Notes

Reaction equation

HRID 1049011 reaction equation
[F:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[CH:9]1([NH2:13])[CH2:12][CH2:11][CH2:10]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH:9]1([NH:13][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 707251-Fluoro-3-iodobenzeneHCID 75645CyclobutylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 61778890HCID 61778890, compoundYield 71.2%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-fluoroiodobenzene (1.0 g, 4.5 mmol), cyclobutylamine (320 μL, 3.8 mmol), Pd2(dba)3 (34 mg, 38 μmol), XantPhos (54 mg, 94 μmol), and sodium tert-butoxide (541 mg, 5.6 mmol) in toluene (10 mL) was degassed with nitrogen then heated at 120° C. for 30 minutes in a microwave reactor. Saturated aqueous NaHCO3 was added and then extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated and purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give cyclobutyl-(3-fluoro-phenyl)-amine (447 mg, 71%). LCMS (m/z, Method A) ES+ 166[M+1]+.

Workup

  1. customwas degassed with nitrogen
  2. additionSaturated aqueous NaHCO3 was added
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (0-50% DCM in cyclohexane)

Sources & evidence

ORD record
ord-ccf04a3dd5a648d1ac54b4d3a33d4137
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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