HCID 58368632, compound → HCID 58368566, compound

HRID 1192572Notes

Reaction equation

HRID 1192572 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]([C:18]#[N:19])=[CH:10][C:9]=2[CH:20]=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH3:22][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]([C:18]#[N:19])=[CH:10][C:9]=2[CH:20]([OH:21])[CH3:22])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58368632HCID 58368632, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58368566HCID 58368566, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a mixture of 8-(3-fluorophenyl)-7-formylquinoline-5-carbonitrile (20 mg, 0.07 mmol) in tetrahydrofuran (1 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (0.12 mL, 0.17 mmol) at −78° C. The reaction was stirred at −78° C. for 30 minutes, quenched with water at −78° C. The mixture was neutralized with 1 N HCl, and then extracted with ethyl acetate. The combined orgagnic layers were washed with brine, dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step (20 mg, 90%). LCMS calculated for C18H14FN2O (M+H)+: m/z=293.1; Found: 293.0.

Workup

  1. customquenched with water at −78° C
  2. extractionextracted with ethyl acetate
  3. washThe combined orgagnic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-97a8d978b7bf4495954be684929dda6d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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