Dibutyltin dichloride → HCID 67971453, compound

HRID 1614901Notes

Reaction equation

HRID 1614901 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]#[C:8][C:9]([CH3:12])([CH3:11])[CH3:10])[S:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][O:18][P:19]1(=[O:26])[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1.CN(C=O)C>[CH3:10][C:9]([CH3:11])([CH3:12])[C:8]#[C:7][C:5]1[S:4][C:3]([C:13]([O:15][CH3:16])=[O:14])=[C:2]([NH:1][CH:22]2[CH2:23][CH2:24][P:19]([O:18][CH3:17])(=[O:26])[CH2:20][CH2:21]2)[CH:6]=1

Participants

7

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 110737321-Methoxyphosphinan-4-one 1-oxideHCID 24989346Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylate

Product 1

HCID 67971453HCID 67971453, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-amino-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate (474 mg, 2 mmol) and 1-Methoxy-1-oxo-1λ5 phosphinan-4-one (390 mg, 2.4 mmol) in THF (1 mL) and DMF (1 mL) was treated with dibutyltin dichloride (60 mg, 0.2 mmol). After 5 min, phenylsilane (272 μL, 2.2 mmol) was added, and the mixture was stirred for one hour at room temperature and then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with 5% LiCl and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using EtOAc:Hexanes as eluent to provide 650 mg (85%) of title compound: MS (m/z) 384.0 [M+H]+; HPLC retention time: 4.463 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic layers were washed with 5% LiCl and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b69e0d05f5ff4c75bd9ddc7e4659e178
Source dataset
uspto-grants-2014_07
Patent number
US08765722B2

Reaction notes

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