Dibutyltin dichloride → HCID 178497914, compound

HRID 416300Notes

Reaction equation

HRID 416300 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([NH2:14])[NH:11][N:10]=2)=[CH:5][CH:4]=1.[CH:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O.[Sn](CCCC)(CCCC)(Cl)Cl.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([NH:14][CH2:15][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 15294Methyl 4-FormylbenzoateHCID 178488696HCID 178488696, compound

Product 1

HCID 178497914HCID 178497914, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of amine 383 (720 mg, 3.79 mmol), methyl 4-formylbenzoate (745 mg, 4.54 mmol), and Bu2SnCl2 (230 mg, 0.76 mmol) in dry THF (5 mL) was stirred at room temperature for 2 hours. It was then treated with PhSiH3 (514 μL, 451 mg, 4.17 mmol) and allowed to stir for another hour at room temperature. The reaction mixture was quenched by addition of MeOH and vigorous stirring for 45 min. It was then concentrated in vacuo and the residue was purified by flash chromatography using the gradient 50-100% EtOAc in hexane to afford the title compound (672 mg, 52% yield). LRMS: (calc) 338.1; (found) 339.2 (M+H1)

Workup

  1. customThe reaction mixture was quenched by addition of MeOH
  2. stirringvigorous stirring for 45 min
  3. concentrationIt was then concentrated in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cef022391d23485eae89d86a4953b620
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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