Tributyltin Chloride → HCID 178448230、化合物

HRID 246097ノート

反応式

HRID 246097 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[C:4]([F:12])[CH:3]=1.[H-].[Na+].C([Mg]Cl)(C)C.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:24]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23])=[N:7][NH:8]2)=[C:4]([F:12])[CH:3]=1

参加物

8

反応物 5

HCID 15096Tributyltin ChlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178418918HCID 178418918、化合物HCID 178505824HCID 178505824、化合物

生成物 1

HCID 178448230HCID 178448230、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-15 °C

実験手順

6-Chloro-4-fluoro-3-iodo-1H-indazole (10.1 g, 34.1 mmol) was dissolved in THF (170 ml). The reaction flask was stirred in a water bath and sodium hydride (60% dispersion, 1.64 g, 40.9 mmol) was added. The mixture was stirred for 15 min then cooled in an ice/salt bath to −15° C. Isopropylmagnesium chloride (2.0 M in THF, 20.6 ml, 41.2 mmol) was added dropwise. After 40 min, tributyltin chloride (11.6 ml, 42.6 mmol) was slowly added and the reaction was allowed to warm to room temperature. After an additional 2 h stirring, ammonium chloride solution and ethyl acetate were added. The layers were separated and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. Evaporation of the solvent provided 6-chloro-4-fluoro-3-tributylstannanyl-1H-indazole as an oil which was used directly in the next step.

後処理

  1. stirringThe mixture was stirred for 15 min
  2. temperatureto warm to room temperature
  3. stirringAfter an additional 2 h stirring
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted once more with ethyl acetate
  6. washThe combined organic layers were washed with sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-093b8c6b071e431c99b8100cffdcde51
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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