Sodium Iodide → HCID 86710087, compound

HRID 1468281Notes

Reaction equation

HRID 1468281 reaction equation
[I-].[Na+].Cl[Si](Cl)(C)C.[F:8][C:9]1([F:38])[CH2:14][CH2:13][CH:12]([CH:15](O)[C:16]2[N:20]3[C:21]([CH3:32])=[CH:22][C:23]([C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[CH:24][C:19]3=[N:18][C:17]=2[C:33]2([CH3:36])[CH2:35][CH2:34]2)[CH2:11][CH2:10]1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.ClCCl.C(#N)C>[F:38][C:9]1([F:8])[CH2:10][CH2:11][CH:12]([CH2:15][C:16]2[N:20]3[C:21]([CH3:32])=[CH:22][C:23]([C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[CH:24][C:19]3=[N:18][C:17]=2[C:33]2([CH3:36])[CH2:34][CH2:35]2)[CH2:13][CH2:14]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6398DichlorodimethylsilaneHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 86710088HCID 86710088, compound

Product 1

HCID 86710087HCID 86710087, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Sodium iodide (121 mg, 0.805 mmol) was suspended in a dichloromethane-acetonitrile (1:1) mixed solvent (0.8 mL). Under ice-cooled condition, dichlorodimethylsilane (52.0 mg, 0.403 mmol) was added, and the mixture was stirred for 20 minutes. The reaction mixture was stirred at room temperature for 30 minutes after adding a dichloromethane solution (0.4 mL) of butyl 3-{(4,4-difluorocyclohexyl) (hydroxy)methyl}-5-methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-7-carboxylate (35.0 mg, 0.0810 mmol) obtained in step 3. Then, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium thiosulfate aqueous solution were added to the reaction mixture, and the mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL). The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→65/35) to give butyl 3-(4,4-difluorocyclohexylmethyl)-5-methyl-2-(1-methylcyclopropyl)imidazo[1,2-a]pyridine-7-carboxylate (24.6 mg, yield 73%).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. filtrationthe mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL)
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→65/35)

Sources & evidence

ORD record
ord-8e9efe1d94fd40ffa756c22c8bf77e2c
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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