Sodium hydride → 2-(5-Chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

HRID 11673Notes

Reaction equation

HRID 11673 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:16])[CH2:14][OH:15])[C@H:9]([CH3:17])[CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][C:26]([Cl:32])=[CH:25][N:24]=1>C1(C)C=CC=CC=1>[Cl:32][C:26]1[CH:27]=[C:28]([N+:29]([O-:31])=[O:30])[C:23]([O:15][CH2:14][C:13]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=3)[CH2:8][C@H:9]2[CH3:17])=[O:16])=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80633312,5-Dichloro-3-nitropyridineHCID 696552871-[4-(4-Fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-hydroxy-ethanone

Product 1

HCID 696557252-(5-Chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanoneYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-hydroxy-ethanone (0.77 g, 2.9 mmol) in dry toluene (30 mL) at 0° C. was added sodium hydride (0.13 g, 3.2 mmol, 60% dispersion in mineral oil). The reaction was stirred for 30 minutes at 0° C. followed by addition of 2,5-dichloro-3-nitro-pyridine (0.60 g, 3.18 mmol) as a solution in toluene (5 mL). The reaction was stirred at ambient temperature overnight. The, reaction was concentrated and chromatographed on silica gel to give the title compound (0.96 g).

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe, reaction
  3. concentrationwas concentrated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-edda315ee14642109c66752a9920736e
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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