Tetrahydrofuran → HCID 86620430, compound

HRID 1907772Notes

Reaction equation

HRID 1907772 reaction equation
[C:1]1([SiH3])[CH:6]=[CH:5]C=CC=1.[F:8][C:9]([F:27])([F:26])[CH:10]=[N:11][CH:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([O-:23])=[O:22])=[CH:19][CH:18]=2)[CH2:13]1.[CH2:28]1COCC1>CCOC(C)=O.C([Sn](Cl)(Cl)CCCC)CCC>[F:27][C:9]([F:8])([F:26])[CH2:10][NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][C:6]([CH3:5])([CH3:1])[CH3:28])=[O:22])=[CH:24][CH:25]=2)[CH2:13]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 12752PhenylsilaneHCID 86620431HCID 86620431, compound

Product 1

HCID 86620430HCID 86620430, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 12688Dibutyltin dichlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dibutyltin dichloride (28 mg, 0.09 mmol) and phenylsilane (365 mg, 3.37 mmol) were added to a suspension of 457 (1.05 g, 3.07 mmol), in THF (6.1 mL). The reaction mixture was stirred for 48 h at room temperature, diluted with AcOEt, washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography to afford the title compound 458 (647 mg, 61% yield) as a white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ce4e475dbd1f4c44b2af01d0820a9a39
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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