Sodium Iodide → HCID 86721406, compound

HRID 869568Notes

Reaction equation

HRID 869568 reaction equation
[I-].[Na+].C[Si](C)(C)Cl.C(#N)C.[F:11][C:12]1[CH:13]=[CH:14][C:15]2=[C:16]([CH:44]=1)[O:17][CH2:18][C:19]1[CH:29]=[C:28]([CH:30](O)[C:31]3[N:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]4=[N:33][C:32]=3[CH2:40][O:41][CH3:42])[CH:27]=[CH:26][C:20]=1/[C:21]/2=[C:22](/[CH3:25])\[C:23]#[N:24]>O.CCCCCC>[F:11][C:12]1[CH:13]=[CH:14][C:15]2=[C:16]([CH:44]=1)[O:17][CH2:18][C:19]1[CH:29]=[C:28]([CH2:30][C:31]3[N:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]4=[N:33][C:32]=3[CH2:40][O:41][CH3:42])[CH:27]=[CH:26][C:20]=1/[C:21]/2=[C:22](/[CH3:25])\[C:23]#[N:24]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 86721407HCID 86721407, compound

Product 1

HCID 86721406HCID 86721406, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

[step 5] To sodium iodide (197 mg, 1.32 mmol) were added trimethylchlorosilane (165 mL, 1.32 mmol) and acetonitrile (69 mL, 1.3 mmol), and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added hexane (0.22 mL). Furthermore, (E)-2-(3-fluoro8-{hydroxy[2-(methoxymethyl)imidazo[1,2-a]pyridin-3-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (100 mg, 0.22 mmol) obtained in step 4 was added, and the mixture was stirred for 1 hr. The reaction was discontinued with water, and the mixture was extracted with chloroform, the extract was washed with saturated sodium thiosulfate aqueous solution, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the obtained reaction residue was purified by silica gel column chromatography (chloroform/methanol=10/1 v/v) to give the title compound (60 mg, 62%).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. extractionthe mixture was extracted with chloroform
  3. washthe extract was washed with saturated sodium thiosulfate aqueous solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained reaction residue
  8. customwas purified by silica gel column chromatography (chloroform/methanol=10/1 v/v)

Sources & evidence

ORD record
ord-c92a9392bba849a5b4911b8d3191d5a6
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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