Dimethylformamide → HCID 178434462, compound

HRID 2074481Notes

Reaction equation

HRID 2074481 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 extracted 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. extractionthe reaction mixture was extracted by ethylacetate twice
  7. washThe combined organic layer was washed with brine once
  8. dry with materialdried over sodium sulfate
  9. customThe crude product was chromatographed with 50% ethylacetate in hexane

Sources & evidence

ORD record
ord-7cb592ccb2634c27a6a98aba5b49d988
Source dataset
uspto-grants-2011_04
Patent number
US07919514B2

Reaction notes

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