HCID 86725322, compound → HCID 86725324, compound

HRID 925210Notes

Reaction equation

HRID 925210 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:12]2[C:13]3[C:14](=[O:22])[C:15]([F:21])([F:20])[CH2:16][C:17]=3[CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Mg]Br>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:12]2[C:13]3[C:14]([OH:22])([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][CH3:25])[C:15]([F:21])([F:20])[CH2:16][C:17]=3[CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 86725322HCID 86725322, compoundHCID 178489560HCID 178489560, compound

Product 1

HCID 86725324HCID 86725324, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a glass vial containing the product from step (b) (130 mg, 0.385 mmol) in diethyl ether (5 ml), 2-methoxyphenyl magnesium bromide (3.85 ml, 1.92 mmol) was added. The reaction mixture was stirred at reflux for 30 minutes. The reaction was cooled to room temperature, quenched with of 10% aqueous NH4Cl (50 ml), and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and the solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes) gave the sub-title compound as a yellow oil (145 mg). MS: ESI (positive): 446 (M+1).

Workup

  1. additionwas added
  2. temperatureat reflux for 30 minutes
  3. customquenched with of 10% aqueous NH4Cl (50 ml)
  4. extractionextracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated in vacuo
  8. customto give the crude product
  9. customPurification
  10. washby silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e1a61930a3214f2e93f19a7400f8cf4e
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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