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

HRID 1839308ノート

反応式

HRID 1839308 の反応式
[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]

参加物

7

反応物 4

HCID 1061PhosphateHCID 15096Tributyltin ChlorideHCID 23448997Methyl imidazo[5,1-b]thiazole-7-carboxylateHCID 86588928Lithium bis(trimethylsilyl)amide hexane

生成物 1

HCID 23449182Methyl 2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole-7-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5baaa9b65e3c4322bf777745abb5ef58
出典データセット
uspto-grants-2004_01
特許番号
US06677331B2

反応ノート

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