Phosphate → Methyl 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole-7-carboxylate

HRID 1839308Notes

Reaction equation

[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[S:15]1[CH:19]=[CH:18][N:17]2[CH:20]=[N:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:16]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC.P([O-])([O-])([O-])=O>C1COCC1.ClCCl>[CH2:1]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[C:19]1[S:15][C:16]2=[C:22]([C:23]([O:25][CH3:26])=[O:24])[N:21]=[CH:20][N:17]2[CH:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution (5 ml) of 0.716 g of tri-n-butylstannyl Chloride in THF was added to a solution (20 ml) of 0.364 g of methyl imidazo[5,1-b]thiazole-7-carboxylate in THF at −70° C. A 1.0 N lithiumbis(trimethylsilyl)amide/n-hexane solution (4.4 ml) was added dropwise thereto at −70° C. The mixture was stirred at −50° C. for 30 min. The reaction solution was added to an ice cold mixed solution composed of 50 ml of 0.2 N phosphate buffer (ph 7) and 50 ml of dichloromethane with stirring. The organic layer was separated, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was subjected to separation and purification by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 0.395 g of the title, compound.

Workup

customat −70° C
stirringwith stirring
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed by distillation
customThe residue was subjected to separation and purification by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)
customto give 0.395 g of the title, compound

Sources & evidence

ORD record: ord-5baaa9b65e3c4322bf777745abb5ef58
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677331B2

Reaction notes

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