Sodium Chloride → 7-(Thiazol-4-yl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 989853Notes

Reaction equation

[S:1]1[CH:5]=[C:4]([C:6]2[N:7]=[CH:8][N:9]3[CH:13]=[CH:12][S:11][C:10]=23)[N:3]=[CH:2]1.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[Cl-].[Na+]>C1COCC1>[S:1]1[CH:5]=[C:4]([C:6]2[N:7]=[CH:8][N:9]3[CH:13]=[C:12]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])[S:11][C:10]=23)[N:3]=[CH:2]1

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 1.01 g of 7-(thiazol-4-yl)imidazo[5,1-b]thiazole in 45 ml of THF was cooled to −70° C. in an argon atmosphere. Tri-n-butylstannyl chloride (1.58 ml) was added thereto. A 1 N lithiumbis(trimethylsilyl)amide/THF solution (11.2 ml) was added dropwise at the same temperature. The mixture was stirred for 30 min. The temperature of the mixture was raised to −30° C. over a period of one hr. A saturated aqueous sodium chloride solution was added thereto, followed by extraction twice with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1). The title compound (294 mg) was obtained from the fraction of Rf=0.5.

Workup

extractionfollowed by extraction twice with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under the reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-74279f7575134af1ac1b68f1ab7a9ba9
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458780B1

Reaction notes

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