Sodium Iodide → HCID 57754607, compound

HRID 227127Notes

Reaction equation

HRID 227127 reaction equation
Br[C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5].O[C@H]1CCCC[C@@H]1NC.[I-:38].[Na+]>O1CCOCC1.[Cu](I)I>[I:38][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 6504200(1S,2S)-2-Methylamino-cyclohexanolHCID 53627950HCID 53627950, compound

Product 1

HCID 57754607HCID 57754607, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

443 mg (1 mmol) of 3-(2-Bromo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one, 9.5 mg (0.05 mmol) of copper iodide, 14.2 mg (0.1 mmol) (1S,2S)-1-hydroxy-2-methylaminocyclohexane and 300 mg (2 mmol) of sodium iodide were mixed in 5 mL of dioxane. The mixture was stirred at 110° C. in a sealed tube for 18 hours. The reaction was quenched by adding 50 mL of water. The mixture was extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of water, 50 mL of sat. brine, dried over magnesium sulfate overnight. The solid was filtered and the filtrate was concentrated to dryness. The crude product was purified with flash chromatography to yield 270 mg of 3-(2-Iodo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one as colorless solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding 50 mL of water
  3. extractionThe mixture was extracted with 50 mL of ethyl acetate
  4. washThe organic layer was washed with 50 mL of water, 50 mL of sat. brine
  5. dry with materialdried over magnesium sulfate overnight
  6. filtrationThe solid was filtered
  7. concentrationthe filtrate was concentrated to dryness
  8. customThe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-e66127fb519b47f68c655646409e7d4b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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