HCID 11338407, compound → HCID 11476994, compound

HRID 1796335Notes

Reaction equation

HRID 1796335 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1.[C:29]1([Mg]Br)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[OH:26])=[CH:27][CH:28]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11338407HCID 11338407, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 11476994HCID 11476994, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-benzaldehyde, prepared as described in Example 52, (100 mg, 0.25 mmol) was dissolved in dry THF and cooled to 0° C. To the solution was added a 1 M solution of PhMgBr in THF (0.63 mL, 0.63 mmol) and the reaction was stirred at 25° C. for 2 h, quenched with water and neutralized with 10% HCl and extracted with EtOAc (100 mL). The EtOAc was washed with brine, dried and stripped in vacuo. The residue was purified by silica gel chromatography (20% EtOAc/hexanes eluent) to give 15 mg {4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-phenyl-methanol as an amorphous solid. mass spec. (AP+): m/z 473 (M+1).

Workup

  1. customquenched with water and neutralized with 10% HCl
  2. extractionextracted with EtOAc (100 mL)
  3. washThe EtOAc was washed with brine
  4. customdried
  5. customThe residue was purified by silica gel chromatography (20% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-d94a12a0fff64229b3692ad239cf58d4
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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