Tetrahydrofuran → HCID 22485195, compound

HRID 2390901Notes

Reaction equation

HRID 2390901 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:17][C:16]=1[Cl:27]>O>[Cl:27][C:16]1[C:15]([CH2:14][OH:13])=[CH:20][CH:19]=[C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:17]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 22484962Methyl 2-chloro-6-phenylpyridine-3-carboxylate

Product 1

HCID 22485195HCID 22485195, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the mixture of lithium aluminum hydride (120 mg, 2.5 mmol) and tetrahydrofuran (10 ml), a mixture of 2-chloro-6-phenyl-nicotinic acid methyl ester (620 mg, 2.5 mmol) synthesized in Example 24 and tetrahydrofuran (2.4 ml) was gradually added under nitrogen atmosphere at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 30 minutes. Water was gradually added dropwise thereto at the same temperature, and the obtained reaction mixture was stirred at room temperature for 1 hour. Impurities were removed by filtration with Celite, and the solvents were evaporated under reduced pressure from the filtrate. The obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=2:1), thereby obtaining the entitled compound (470 mg, 86%).

Workup

  1. additionwas gradually added under nitrogen atmosphere at 0° C. (an outer temperature), and
  2. customthe obtained reaction mixture
  3. customat the same temperature, and the obtained reaction mixture
  4. stirringwas stirred at room temperature for 1 hour
  5. customImpurities were removed by filtration with Celite
  6. customthe solvents were evaporated under reduced pressure from the filtrate
  7. customThe obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-fefb0ed306bb440197df444b95381c0c
Source dataset
uspto-grants-2012_09
Patent number
US08273885B2

Reaction notes

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