Sodium hydride → HCID 90013565, compound

HRID 589010Notes

Reaction equation

HRID 589010 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[Br:1][C:2]1[C:7]([CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:10][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 90013746HCID 90013746, compound

Product 1

HCID 90013565HCID 90013565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 2-(2-bromopyridin-3-yl)-1-phenylethanol (2.5 g, 9.0 mmol) in anhydrous DMF (10 mL) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.54 g, 13 mmol) in anhydrous DMF (10 mL) at 0° C., and the resulting mixture was stirred for 30 min. Methyl bromoacetate (1.03 mL, 10.7 mmol) was added, and the contents were warmed to 23° C. and stirred for 30 min, then partitioned between ethyl acetate and water (2×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in petroleum ether to give the title compound. MS: m/z=352.0 (M+1).

Workup

  1. stirringstirred for 30 min
  2. custompartitioned between ethyl acetate and water (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-a0e13991f6454f048533baf46500d032
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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