Dimethylformamide → HCID 58006149, compound

HRID 215914Notes

Reaction equation

HRID 215914 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[N:9]([CH3:11])[CH3:10].CN(CCN(C)C)C.[Li]CCCC.CN([CH:32]=[O:33])C>C1COCC1.O>[CH3:11][N:9]([CH3:10])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[C:7]=1[CH:32]=[O:33]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 58006280HCID 58006280, compoundHCID 178418339Butyllithium

Product 1

HCID 58006149HCID 58006149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of Compound 71 (2.8 g, 13.5 mmol) in THF (10 mL) was added TMEDA (1.88 g, 16.2 mmol) followed by n-BuLi (2.5 M solution in hexane, 6.5 mL, 16.2 mmol). The mixture was stirred for 30 min at room temperature then DMF (1.48 g, 20.25 mmol) was added and the solution stirred for 3 h at room temperature. The reaction was then diluted with water (20 mL), and the product was extracted with EtOAc (3×50 mL). The organic layers were combined and washed with brine, and dried (MgSO4), and filtered, and the solvent was removed under reduced pressure. After silica gel chromatography, the product (Compound 72) was obtained as an oil.

Workup

  1. stirringthe solution stirred for 3 h at room temperature
  2. extractionthe product was extracted with EtOAc (3×50 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e366b38e02e3492f835bf2851f802761
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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