Water → HCID 56925649, compound

HRID 2175462Notes

Reaction equation

HRID 2175462 reaction equation
Br[C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][C:10]([CH3:13])([CH3:12])[O:11][C:5]2=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:22]=[O:23])C.O>C1COCC1>[CH3:12][C:10]1([CH3:13])[O:11][C:5]2[C:6](=[N:7][C:2]([CH:22]=[O:23])=[CH:3][CH:4]=2)[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 56925648HCID 56925648, compoundHCID 178418339Butyllithium

Product 1

HCID 56925649HCID 56925649, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 23 (200 mg, 0.83 mmol) in anhydrous THF (5 mL) at −78° C. was added BuLi (2.5M, 0.35 mL) and stirred for 35 minutes, then DMF (0.08 mL, 0.1 mmol) was added dropwise. The reaction was stirred at −78° C. for 30 additional minutes. Water (3 mL) was added to quench the reaction and was extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography; 20:1 Hx/EtOAc. To give the product as a yellowish solid (23% yield). 1H NMR δ 1.53 (s, 6H), 6.01 (d 1H, J=10.4), 6.58 (d, 1H, J=10.4), 7.13 (d, 1H, J=8.4), 7.77 (d, 1H, J=8.4), 9.93 ppm (s, 1H). 13C NMR δ 28.8, 78.7, 123.0, 123.3, 123.4, 136.3, 145.8, 153.7, 191.9 ppm

Workup

  1. stirringThe reaction was stirred at −78° C. for 30 additional minutes
  2. customto quench
  3. customthe reaction
  4. extractionwas extracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-0bbe8cb644b44f39b3b680f3cecefc69
Source dataset
uspto-grants-2015_06
Patent number
US09062072B2

Reaction notes

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