Tributyltin Chloride → HCID 178448228、化合物

HRID 246312ノート

反応式

HRID 246312 の反応式
[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][N:14]=[C:13]2I)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C([Mg]Cl)(C)C.[CH2:27]([Sn:31]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34][CH2:35][CH3:36])Cl)[CH2:28][CH2:29][CH3:30]>C1COCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][N:14]=[C:13]2[Sn:31]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:27][CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 15096Tributyltin ChlorideHCID 24758Sodium hydrideHCID 178418918HCID 178418918、化合物HCID 178455421HCID 178455421、化合物

生成物 1

HCID 178448228HCID 178448228、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a round-bottomed flask, 7-(tert-butyl-dimethyl-silanyloxymethyl)-3-iodo-1H-indazole (200 mg, 0.52 mmol) was dissolved in THF (2.8 ml) and sodium hydride (60% in mineral oil, 25 mg, 0.63 mmol) was added. The reaction mixture was stirred at room temperature for 10 min then cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.36 ml, 0.72 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 30 min then tributylchlorostannane (0.16 ml, 0.59 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 2.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 7-(tert-butyl-dimethyl-silanyloxymethyl)-3-tributylstannanyl-1H-indazole as a yellow oil which was used without further purification.

後処理

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at −16° C. for 30 min
  3. temperatureto warm to room temperature
  4. stirringstirred for 2.5 h
  5. customthen quenched with saturated aqueous NH4Cl
  6. extractionextracted with EtOAc (2×)
  7. washThe organic layers were washed with water and brine
  8. dry with materialthen dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-c4a28bd461a2440f83bc7b2096cfb94c
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

読み込み中…