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

HRID 989843ノート

反応式

HRID 989843 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収率 42%

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)

出典と根拠

ORDレコード
ord-b3aa013f54a04ce09ec738a32eb918f4
出典データセット
uspto-grants-2002_10
特許番号
US06458780B1

反応ノート

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