2-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde → HCID 58318628, compound

HRID 473438Notes

Reaction equation

HRID 473438 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([CH:21]=[O:22])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)(=[O:4])=[O:3].[CH3:23][Mg]Br>C1COCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([CH:21]([OH:22])[CH3:23])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 583185932-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 58318628HCID 58318628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude of 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde (1.0 g, 3.2 mmol) in THF (25 mL) was added methyl magnesium bromide (3.2 mL, 9.6 mmol) at 0° C. The reaction mixture was stirred for 2 h at same temperature. The reaction mixture was quenched with satd solution of ammonium chloride and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give 1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanol: LC-MS (ESI) m/z 329.0 [M+H]+. It was carried on crude for next step.

Workup

  1. customThe reaction mixture was quenched with satd solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d3df213c8cb48d493e9eea35806ffc0
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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