Triethylsilane → HCID 68754450, compound

HRID 2409962Notes

Reaction equation

HRID 2409962 reaction equation
O[CH:2]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:23][O:22][C:18]1[CH:17]=[C:16]2[C:21]([C:13]([CH2:2][C:3]3[S:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=3)=[C:14]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 68757116HCID 68757116, compound

Product 1

HCID 68754450HCID 68754450, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to an ice-cooled solution of ethyl 2-[hydroxy(6-methoxy-2-phenyl-1H-indol-3-yl)methyl]thiazole-4-carboxylate (69.0 mg) and triethylsilane (0.135 mL) in methylene chloride (1.7 mL) was slowly added dropwise a boron trifluoride diethyl ether complex (0.107 mL). After stirring for 10 minutes, the mixture was stirred at room temperature for additional 15 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (17.0 mg). 1H-NMR (CDCl3) δ ppm: 1.43 (3H, t, J=7.2 Hz), 3.87 (3H, s), 4.45 (2H, q, J=7.2 Hz), 4.61 (2H, s), 6.79 (1H, dd, J=2.1, 8.7 Hz), 6.93 (1H, d, J=2.1 Hz), 7.30-7.60 (6H, m), 7.99 (1H, s), 8.13 (1H, br s).

Workup

  1. additionwas slowly added dropwise a boron trifluoride diethyl ether complex (0.107 mL)
  2. stirringthe mixture was stirred at room temperature for additional 15 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1def43abd08a4db593ba5df2bfbb351e
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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