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

HRID 989853ノート

反応式

HRID 989853 の反応式
[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

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 15096Tributyltin ChlorideHCID 234491117-(Thiazol-4-yl)imidazo[5,1-b]thiazoleHCID 23714775LiHMDS tetrahydrofuran

生成物 1

HCID 234492577-(Thiazol-4-yl)-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-74279f7575134af1ac1b68f1ab7a9ba9
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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