Ethyl Acetate → HCID 11013897, compound

HRID 1068709Notes

Reaction equation

HRID 1068709 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:27](OC(C)(C)C)=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.I[Si](C)(C)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)(Cl)Cl>[F:25][C:23]([F:24])([F:26])[S:20]([NH:19][CH2:18][CH2:17][CH2:16][N:15]1[CH2:14][C:10]2[N:9]3[C:5](=[CH:6][N:7]=[C:8]3[CH:13]=[CH:12][CH:11]=2)[C:27]1=[O:28])(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 21190110HCID 21190110, compound

Product 1

HCID 11013897HCID 11013897, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.16 g (2.00 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-[3-(trifluoromethanesulfonamido)propan-1-yl]aminomethyl]imidazo[1,2-a]pyridine in 25 ml of chloroform was added dropwise 0.57 ml (4.00 mmol) of iodotrimethylsilane at room temperature. The reaction mixture was stirred for 15 minutes, which was then poured into ice-water, followed by neutralization with a saturated aqueous solution of sodium hydrogencarbonate. This solution was extractedith 150 ml of ethyl acetate. The organic layer was washed with 100 ml of a 1.0N aqueous solution of sodium thiosulfate, then with 100 ml of a saturated aqueous saline solution. The organic layer was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1) to give 397 mg of the desired compound (54.8%, pale yellow solid).

Workup

  1. washThe organic layer was washed with 100 ml of a 1.0N aqueous solution of sodium thiosulfate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified by silicagel column chromatography (eluent: chloroform/methanol=20:1)

Sources & evidence

ORD record
ord-38a9f668a1eb49c7992699c90a484ea6
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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