Dimethylformamide → HCID 178437999, compound

HRID 237404Notes

Reaction equation

HRID 237404 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.CCCCC.CN(C)[CH:25]=[O:26]>C1COCC1>[CH2:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH:25]=[O:26])[CH:3]=2)[NH:7][N:6]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 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 7A) in THF (300 ml) was cooled to −78° C. At this temperature, a 1.7 M solution of tert-butyllithium in n-pentane (63.1 ml, 107 mmol) was 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-88259785bac34dee90c55d7e96394b2b
Source dataset
uspto-grants-2014_02
Patent number
US08642595B2

Reaction notes

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