Dimethylformamide → HCID 178437999, compound

HRID 1521786Notes

Reaction equation

HRID 1521786 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][CH3:12].C([Li])(C)(C)C.CN(C)[CH:20]=[O:21]>C1COCC1>[CH2:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH:20]=[O:21])[CH:3]=2)[NH:7][N:6]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 178418306HCID 178418306, compoundHCID 178437989HCID 178437989, compound

Product 1

HCID 178437999HCID 178437999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.90 g (30.7 mmol) 5-bromo-3-ethyl-1H-indazole (Example 16A) in THF (300 ml) was cooled to −78° C. At this temperature, 63.1 ml (107 mmol) of tert-butyllithium solution (1.7 M in n-pentane) were slowly added. The mixture was stirred at −78° C. for 30 minutes before N,N-dimethylformamide (80.0 ml) was slowly added. The cooling bath was removed, and stirring was continued until room temperature was reached. Then, water (250 ml) was added carefully. The mixture was extracted several times with ethyl acetate (500 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to yield 4.5 g (84% of th.) of the crude title compound which was used in the next step without further purification.

Workup

  1. additionwas slowly added
  2. customThe cooling bath was removed
  3. customwas continued until room temperature
  4. additionThen, water (250 ml) was added carefully
  5. extractionThe mixture was extracted several times with ethyl acetate (500 ml)
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-deb3f0d1dd6a4fb7bb462b33a52f6537
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

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