HCID 117798829, compound → HCID 12080198, compound

HRID 1844325Notes

Reaction equation

HRID 1844325 reaction equation
C1(S([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[N:11]=2)(=O)=O)C=CC=CC=1.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[C:25]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:17])=[O:18])[N:11]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 117798829HCID 117798829, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 12080198HCID 12080198, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of bis-(phenylsulfonyl)pyridine 4d (1.0 g, 2.78 mmol) in 10 mL THF at room temperature is charged 1.0 M PhMgBr (5.56 ml, 2.0 equiv) slowly over a period of 10 min. The progress of the reaction is monitored by LC-MS. Upon complete consumption of the starting material (about 2 h), the mixture is quenched with MeOH (2 mL). The crude mixture is then evaporated to dryness, and the product is isolated by flash column chromatography (silica gel, 15% ethyl acetate in hexanes) and dried to yield 656 mg of 3e as a white solid, 80% yield. 1H NMR (400 MHz, CDCl3) δ 8.14-8.08 (m, 3H), 7.95-7.91 (m, 3H), 7.83-7.86 (m, 1H), 7.62-7.51 (m, 3H), 7.46-7.40 (m, 3H); 13C NMR (100 MHz, CDCl3) δ 158.7, 158.0, 138.9, 138.7, 137.1, 133.7, 130.0, 129.2, 128.9, 128.8, 127.0, 123.1, 119.8.

Workup

  1. customUpon complete consumption of the starting material (about 2 h)
  2. customthe mixture is quenched with MeOH (2 mL)
  3. customThe crude mixture is then evaporated to dryness
  4. customthe product is isolated by flash column chromatography (silica gel, 15% ethyl acetate in hexanes)
  5. customdried

Sources & evidence

ORD record
ord-96067acb53da49a4876ada23c5d5a8c0
Source dataset
uspto-grants-2015_02
Patent number
US08946418B1

Reaction notes

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