1-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone → 2-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol

HRID 2193033Notes

Reaction equation

HRID 2193033 reaction equation
[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16](=[O:18])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4].[CH3:24][Mg]Br>O1CCCC1>[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([OH:18])([CH3:24])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 593755411-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 593756702-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone (59 mg, 0.19 mmol) in tetrahydrofuran (2.0 ml) was added methylmagnesium bromide (1.4 M in toluene/THF 75:25; 0.202 ml, 0.283 mmol) dropwise at −78° C. The cooling bath was removed, and the resulting suspension was allowed to warm to room temperature. The reaction mixture was stirred for 30 minutes, and then quenched with saturated aqueous ammonium chloride (5 mL). Water was added, and the mixture extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude solid that was adsorbed on to silica gel and purified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient to afford 2-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol. LRMS (ESI) calc'd for (C19H21FN2O2) [M+H]+, 329.2; found 329.1.

Workup

  1. customThe cooling bath was removed
  2. customquenched with saturated aqueous ammonium chloride (5 mL)
  3. additionWater was added
  4. extractionthe mixture extracted with EtOAc
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude solid that
  8. custompurified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-54cd3a06399c45218cd3f88185986dba
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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