Sodium hydride → 1-{3-[6-(2-Fluorophenyl)pyridin-3-yl]propyl}pyridin-2(1H)-one

HRID 1896694Notes

Reaction equation

HRID 1896694 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[N:18][CH:19]=1>CN(C=O)C>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[N:18]=[CH:19][C:14]([CH2:13][CH2:12][CH2:11][N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[O:3])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 691059795-(3-Bromopropyl)-2-(2-fluorophenyl)pyridineHCID 178516071HCID 178516071, compound

Product 1

HCID 160366511-{3-[6-(2-Fluorophenyl)pyridin-3-yl]propyl}pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.2 mg (0.18 mmol) of sodium hydride (55% suspension in mineral oil) were added to 17.8 mg (0.19 mmol) of 2-hydroxypyridine in 5 ml of DMF, and the mixture was stirred at room temperature for 30 min. Subsequently, 50 mg (0.17 mmol) of 5-(3-bromopropyl)-2-(2-fluorophenyl)pyridine were added. The reaction mixture was stirred for 4 h, concentrated, admixed with water and extracted with methylene chloride. The organic phase was separated and concentrated, and the residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA) Yield: 11 mg (22%).

Workup

  1. stirringThe reaction mixture was stirred for 4 h
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA) Yield: 11 mg (22%)

Sources & evidence

ORD record
ord-16e6a4a36cdd4cdfa2fa255406b2a0d4
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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