Lithium Hexamethyldisilazide → 7-chloro-N-(1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706559ノート

反応式

HRID 706559 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13]CC)=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH:16]([C:19]1[N:24]=[C:23]([CH2:25][N:26]2[C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([NH2:35])[C:29]=3[C:28]([CH3:36])=[N:27]2)[CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH3:17].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:35][C:30]3[CH:31]=[CH:32][CH:33]=[C:34]4[C:29]=3[C:28]([CH3:36])=[N:27][N:26]4[CH2:25][C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:16]([CH3:17])[CH3:18])[N:24]=3)=[O:13])=[CH:9][N:10]=[C:4]2[CH:3]=1

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 67107280Ethyl 7-chloroimidazo[1,2-A]pyridine-3-carboxylateHCID 679746421-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine

生成物 1

HCID 679758637-chloro-N-(1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A round bottom flask containing ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate (15.22 g, 67.8 mmol) and 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine (Preparation D; 19.0 g, 67.8 mmol) in 130 mls of THF was chilled to 0° C. LiHMDS (1M in THF, 149 mls, 149 mmol) was then added by syringe over a 15 minute period. Once the addition was complete, the reaction mixture was stirred at 0° C. for 15 minutes, and then quenched with saturated ammonium chloride (250 mls). This mixture was then extracted two times with EtOAc, the extracts were dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (100% EtOAc) afforded 18.6 g (60%) of the title compound.

後処理

  1. additionOnce the addition
  2. customquenched with saturated ammonium chloride (250 mls)
  3. extractionThis mixture was then extracted two times with EtOAc
  4. dry with materialthe extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c203f8518e814a568377f010b095caf9
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

読み込み中…