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Lithium hexamethyldisilazane → 7-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79441
ノート
印刷プレビュー

反応式

HRID 79441 の反応式
[CH2:1]([C:3]1[C:11]2[C:10]([NH2:12])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]([CH2:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=2)[N:4]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41](OC)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1>C1COCC1.CO.C(Cl)Cl>[Br:31][C:32]1[CH:37]=[CH:36][N:35]2[C:38]([C:41]([NH:12][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]4[C:11]=3[C:3]([CH2:1][CH3:2])=[N:4][N:5]4[CH2:13][C:14]3[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[N:15]=3)=[O:42])=[CH:39][N:40]=[C:34]2[CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 2733832Lithium hexamethyldisilazaneHCID 67259752Methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylateHCID 672598083-Ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine

生成物 1

HCID 672612817-bromo-N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 80.9%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution 3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (328 mg, 1.22 mmol) in anhydrous THF (3 mL) was added under a nitrogen atmosphere at ambient temperature lithium bis(trimethylsilyl)amide (1.0 M in THF, 1.15 mL). The resulting mixture was stirred at ambient temperature for 10 minutes, then added dropwise to a chilled (ice-water bath) solution of methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (140 mg, 0.55 mmol) in anhydrous THF (3 mL). The cold bath was removed, and the reaction mixture was allowed to warm to ambient temperature, and quenched with water. The resulting suspension was extracted thoroughly with DCM, the combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH-DCM as eluent to afford 219 mg of desired product as a yellow solid.

後処理

  1. additionadded dropwise to
  2. customThe cold bath was removed
  3. temperatureto warm to ambient temperature
  4. customquenched with water
  5. extractionThe resulting suspension was extracted thoroughly with DCM
  6. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto afford the crude product

出典と根拠

ORDレコード
ord-f75a56197e3d4287b252b3ec5dd6f04d
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841455B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート