Potassium Phosphate, Tribasic → HCID 86686006, compound

HRID 2277715Notes

Reaction equation

HRID 2277715 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2([CH3:13])[CH3:12].[I:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](I)[CH:20]=1.[C@H]1(N)CCCC[C@@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:19]1[CH:18]=[N:17][CH:16]=[C:15]([I:14])[CH:20]=1)[C:5]2([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 4793071,2-Diaminocyclohexane, (+)-HCID 51102003,5-diiodopyridineHCID 71743949HCID 71743949, compound

Product 1

HCID 86686006HCID 86686006, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-12) (390 mg, 2 mmol), 3,5-diiodo-pyridine (662 mg, 2 mmol), CuI (38 mg, 0.2 mmol), (1S,2S)-cyclohexane-1,2-diamine (45 mg, 0.4 mmol) and K3PO4 (888 mg, 4 mmol) were dissolved in dioxane (10 mL). The reaction mixture was heated at 110° C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (25 mL×2). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (495 mg, 62%) as a white solid. MS: 399.0 (M+H+).

Workup

  1. extractionextracted with EtOAc (25 mL×2)
  2. washThe combined organic layers were washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient)

Sources & evidence

ORD record
ord-6d8658aaa1ac419dac6c7410990ba204
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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