HCID 58318611, compound → HCID 58318644, compound

HRID 473406Notes

Reaction equation

HRID 473406 reaction equation
[CH3:1][Mg]Br.[F:4][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>C1COCC1>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([CH:21]([OH:22])[CH3:1])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1

Participants

4

Reactant 2

HCID 58318611HCID 58318611, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58318644HCID 58318644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (2M in diethyl ether, 2.38 mL, and 4.76 mmol) was added dropwise to the solution of 2-(2-fluorophenyl)-1,5-naphthyridine-3-carbaldehyde (600 mg, 4.76 mmol) in THF (60 mL) at −0° C. After completion of reaction, the reaction mixture was quenched with saturated NH4Cl solution and ethyl acetate, and then filtered through Celite™. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give an oily mass. The oily mass was then purified by silica gel column chromatography using 30% of ethyl acetate and hexane as eluent to give 1-(2-(2-fluorophenyl)-1,5-naphthyridin-3-yl)ethanol as a yellow oil: 1H-NMR (CDCl3) δ: 1.3 (s, 3H), 5.0 (brs, 1H), 7.7-7.2 (m, 5H), 8.4 (d, 1H), 8.8 (s, 1H), 9.0 (s, 1H).

Workup

  1. customAfter completion of reaction
  2. customthe reaction mixture was quenched with saturated NH4Cl solution and ethyl acetate
  3. filtrationfiltered through Celite™
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was back extracted with ethyl acetate
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give an oily mass
  9. customThe oily mass was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f69dd90928644ea8894bb33d2142d0f
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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