N,N'-Dimethylethylenediamine → HCID 59375096, compound

HRID 1811011Notes

Reaction equation

HRID 1811011 reaction equation
[F:1][C:2]1[C:3](I)=[N:4][CH:5]=[CH:6][C:7]=1[I:8].[C:10]1(=[O:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[F:1][C:2]1[C:3]([N:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[O:19])=[N:4][CH:5]=[CH:6][C:7]=1[I:8]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10199PhthalimidineHCID 11430Potassium CarbonateHCID 99979273-FLUORO-2,4-DIIODOPYRIDINE

Product 1

HCID 59375096HCID 59375096, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110° C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) δ 7.86-8.06 (2 H, m), 7.41-7.71 (4 H, m), 5.04 (2 H, s). Mass spectrum m/z 354.9 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (
  6. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

Sources & evidence

ORD record
ord-acf015592d0143889f12118095992fe2
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

Loading…