Sodium Iodide → HCID 86721401, compound

HRID 869563Notes

Reaction equation

HRID 869563 reaction equation
[I-].[Na+].Cl[Si](Cl)(C)C.[Cl:8][C:9]1[C:10]2[N:11]([C:15]([CH:21](O)[C:22]3[CH:41]=[CH:40][C:25]4/[C:26](=[C:36](/[CH3:39])\[C:37]#[N:38])/[C:27]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:28]=5[O:29][CH2:30][C:24]=4[CH:23]=3)=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl.CC(C)=O>[Cl:8][C:9]1[C:10]2[N:11]([C:15]([CH2:21][C:22]3[CH:41]=[CH:40][C:25]4/[C:26](=[C:36](/[CH3:39])\[C:37]#[N:38])/[C:27]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:28]=5[O:29][CH2:30][C:24]=4[CH:23]=3)=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6398DichlorodimethylsilaneHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 86721402HCID 86721402, compound

Product 1

HCID 86721401HCID 86721401, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

[step 4] Sodium iodide (4.63 g, 30.9 mmol) was suspended in a mixed solution of dichloromethane (15 mL)-acetone (15 mL), dichlorodimethylsilane (1.84 mL, 15.4 mmol) was added under ice-cooling, and the mixture was stirred for 15 min. Under ice-cooling, a solution (15 mL) of (E)-2-{8-[(8-chloro-2-cyclopropylimidazo[1,2-a]pyridin-3-yl)(hydroxy)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (1.5 g, 3.09 mmol) obtained in step 3 in dichloromethane was added, and the mixture was stirred at room temperature for 30 min. To the mixture were added 10% aqueous sodium thiosulfate solution (50 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL), and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue was added isopropylalcohol (15 mL)-diisopropyl ether (15 mL), and the precipitated crystals were collected by suction filtration to give the title compound (1.4 g, 97%).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperatureUnder ice-cooling
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. extractionthe mixture was extracted 3 times with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionTo the obtained residue was added isopropylalcohol (15 mL)-diisopropyl ether (15 mL)
  9. filtrationthe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-f54924fe50ac482cbb826fb6cb1ddba4
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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