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

HRID 989853노트

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HRID 989853 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-74279f7575134af1ac1b68f1ab7a9ba9
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458780B1

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