HCID 57500733, compound → HCID 58524640, compound

HRID 1678800Notes

Reaction equation

HRID 1678800 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[N:19]/[S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])=[CH:14][CH:13]=1)=[N:7]2.[CH3:32][Mg]Br>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH3:32])=[CH:14][CH:13]=1)=[N:7]2

Participants

4

Reactant 2

HCID 57500733HCID 57500733, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58524640HCID 58524640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{(1E)-[4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]methylene}-2-methylpropane-2-sulfinamide (34-1, 4.53 g, 10.1 mmol) in methylene chloride (100 mL) was added methyl magnesium bromide (30 mL, 42.0 mmol, 1.4M in 75:25 toluene:THF) at −10° C. After 30 minutes, the reaction was quenched by addition of saturated ammonium chloride solution (while maintaining the temperature below 0° C.) and extracted with methylene chloride. The combined organics were washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a pale yellow solid. MS (M+H+): calculated=464.03, observed=464.2

Workup

  1. customthe reaction was quenched by addition of saturated ammonium chloride solution (
  2. temperaturewhile maintaining the temperature below 0° C.) and
  3. extractionextracted with methylene chloride
  4. washThe combined organics were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c20d4e7f2f094a398f3d03c21129d749
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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