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 706559노트

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HRID 706559 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c203f8518e814a568377f010b095caf9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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