Trimethylsilyl iodide → HCID 21190141, compound

HRID 1068766Notes

Reaction equation

HRID 1068766 reaction equation
OC[C:3]1[N:7]2[C:8]([CH2:12][N:13]([C:25](OC(C)(C)C)=O)[CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=1.C[Si](I)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:23][C:21]([F:24])([F:22])[S:18]([NH:17][CH2:16][CH2:15][CH2:14][N:13]1[CH2:12][C:8]2[N:7]3[C:3](=[CH:4][N:5]=[C:6]3[CH:11]=[CH:10][CH:9]=2)[CH2:25]1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190174HCID 21190174, compound

Product 1

HCID 21190141HCID 21190141, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 233 mg (0.50 mmol) of 3-hydroxymethyl-5-[N-tert-butoxycarbonyl-N-(3-trifluoromethanesulfonamidopropan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in 5.0 ml of chloroform was added 0.36 ml (2.50 mmol) of trimethylsilyl iodide. The mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into ice-water, which was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and extracted of the desired compound with 50 ml of chloroform. The organic layer was washed with 50 ml of a saturated aqueous saline solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1) to afford 109 mg of the desired compound (62.8%, a pale yellow liquid).

Workup

  1. extractionextracted of the desired compound with 50 ml of chloroform
  2. washThe organic layer was washed with 50 ml of a saturated aqueous saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-4eca27f092da405497ccf65f27cb05af
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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