HCID 67316502, compound → HCID 67316245, compound

HRID 1819617Notes

Reaction equation

HRID 1819617 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[N:18]=2)=[C:9]1[CH3:28])([CH3:4])([CH3:3])[CH3:2].[CH3:30][Mg+].[Br-]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2([CH3:30])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[NH:18]2)=[C:9]1[CH3:28])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67316502HCID 67316502, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 67316245HCID 67316245, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

The product of example 3, step b) (1.0 g, 2.44 mmol) was dissolved in 40 mL toluene and cooled to 0° C. Me3AI (1.83 mL of 2 M solution in toluene) was slowly added and the reaction was stirred for 45 minutes at 0° C. MeMgBr (3.5 mL of 1.4 M solution) was added and the reaction was allowed to warn to rt. The reaction was quenched with saturated NH4Cl then partitioned between water and EtOAc. The organic layer was dried over MgSO4 and the crude product was purified by silica gel chromatography (EtOAc/Hex) to give 450 mg of the sub-title compound.

Workup

  1. customto warn to rt
  2. customThe reaction was quenched with saturated NH4Cl
  3. customthen partitioned between water and EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe crude product was purified by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-74326df857ad48b48e48012493cd4955
Source dataset
uspto-grants-2009_10
Patent number
US07601749B2

Reaction notes

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