Tetrahydrofuran → HCID 58300058, compound

HRID 79122Notes

Reaction equation

HRID 79122 reaction equation
FC(F)(F)S(O[C:7]1[C:12]2[N:13]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:14]3[N:15]=[C:16]([NH2:20])[N:17]=[CH:18][C:19]=3[C:11]=2[CH:10]=[CH:9][N:8]=1)(=O)=O.[CH2:28]1COCC1.C[Mg]Br>CN1CCCC1=O>[CH:21]1([N:13]2[C:14]3[N:15]=[C:16]([NH2:20])[N:17]=[CH:18][C:19]=3[C:11]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:28])[C:12]2=3)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 58299622HCID 58299622, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58300058HCID 58300058, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A flame-dried two-necked flask was charged under argon with compound 86 (0.100 g, 0.25 mmol), ferric acetylacetonate (0.0044, 0.012 mmol), THF (2 ml) and N-methylpyrrolidone (0.1 ml). Methylmagnesium bromide (0.27 g, 2.2 mmol, 3M in ether) was added via syringe to the resulting red solution. A yellow precipitate formed immediately. The reaction was stirred at room temperature for 30 min and quenched with 5% NaHCO3, then extracted into DCM The resulting organic solution was washed with brine, dried and concentrated. Purification by flash chromatography (10% methanol/DCM/1% NH4OH) gave compound 87 as a light yellow solid (0.036 g, 54%). LCMS-ESI (POS), M/Z, M+1: Found 268.1, calculated 268.2.

Workup

  1. customA yellow precipitate formed immediately
  2. customquenched with 5% NaHCO3
  3. extractionextracted into DCM The resulting organic solution
  4. washwas washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification by flash chromatography (10% methanol/DCM/1% NH4OH)

Sources & evidence

ORD record
ord-cd4f19cc64c74f979cbe5f77a2a05fa6
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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