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 706559Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-c203f8518e814a568377f010b095caf9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174981B2

Reaction notes

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