Dimethylformamide → HCID 178434462, compound

HRID 899416Notes

Reaction equation

HRID 899416 reaction equation
[Li]C(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:15]([CH3:16])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1.CN([CH:20]=[O:21])C>C1COCC1>[CH3:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([CH:20]=[O:21])[CH:8]=2)[NH:13][N:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 178418306HCID 178418306, compoundHCID 178434433HCID 178434433, compound

Product 1

HCID 178434462HCID 178434462, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80 ml anhydrous THF were charged into a 250 ml round bottom flask and was chilled to −78° C. t-BuLi (1.70 M in THF, 17.6 ml, 30 mmol) was added to the flask via syringe. After stirring for 5 min, 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (2.12 g,10 mmol) was added dropwise via syringe. After 30 min, DMF (3.65 g, 50 mmol) in 20 ml THF was added dropwise and the mixture was stirred for overnight. The reaction was quenched by saturated aqueous ammonium chloride. After evaporating the excess THF, the reaction mixture was extracrted by ethylacetate twice. The combined organic layer was washed with brine once and dried over sodium sulfate. The crude product was chromatographed with 50% ethylacetate in hexane to afford the desired product (0.23 g, y=20.5%).

Workup

  1. additionwas added to the flask via syringe
  2. waitAfter 30 min
  3. stirringthe mixture was stirred for overnight
  4. customThe reaction was quenched by saturated aqueous ammonium chloride
  5. customAfter evaporating the excess THF
  6. washThe combined organic layer was washed with brine once
  7. dry with materialdried over sodium sulfate
  8. customThe crude product was chromatographed with 50% ethylacetate in hexane

Sources & evidence

ORD record
ord-a1b8a868ad4447aaaf5ce3949c44fdbf
Source dataset
uspto-grants-2008_04
Patent number
US07354944B2

Reaction notes

Loading…