Aluminium lithium hydride → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79327Notes

Reaction equation

HRID 79327 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24](OCC)=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([CH2:24][OH:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67260084ethyl 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 67259564N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamideYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylate (201 mg, 0.417 mmol; prepared as in Example 23) in THF (20 mL) was added lithium aluminum hydride (47.4 mg, 1.25 mmol). The reaction mixture was stirred overnight, quenched with sodium sulfate decahydrate, filtered through Celite and the filter pad was washed with EtOAc. The filtrate was concentrated under reduced pressure to give the product (156 mg).

Workup

  1. customquenched with sodium sulfate decahydrate
  2. filtrationfiltered through Celite
  3. washthe filter pad was washed with EtOAc
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a1df8f37ea8489db2984cc51ec9b98b
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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