Nitrogen → HCID 86596910, compound

HRID 2251870Notes

Reaction equation

HRID 2251870 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.N#N.[F:15][C:16]1[N:30]=[CH:29][CH:28]=[CH:27][C:17]=1[C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19].CN([CH:34]=[O:35])C>C1COCC1>[F:15][C:16]1[N:30]=[CH:29][CH:28]=[C:27]([CH:34]=[O:35])[C:17]=1[C:18]([N:20]([CH:21]([CH3:22])[CH3:23])[CH:24]([CH3:25])[CH3:26])=[O:19]

Participants

7

Reactant 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 69031022HCID 69031022, compoundHCID 178418339Butyllithium

Product 1

HCID 86596910HCID 86596910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylamine (1.7 mL, 12.2 mmol) in THF (50 mL) at −78° C. was added n-BuLi (6.1 mL, 2.0 M hexanes) dropwise under N2. The reaction was stirred for 30 min and 2-fluoro-N,N-diisopropyl-nicotinamide (2.75 g, 12.2 mmol) was added dropwise in a solution of THF (15 mL). The reaction was stir for 1 h, then DMF (3 mL, 36 mmol, 3 eq) was added in one portion. The reaction was stirred at −78° C. for 5 min then warmed to RT over 1 h. The reaction was quenched with NH4Cl (saturated, 100 mL), and extracted with EtOAc (2×100 mL). The combined organics were washed with brine (saturated, 200 mL), dried with Na2SO4, and purified by passing through a plug of SiO2to give pure title compound as a white solid. MS (ES+): 253.1 (M+H)+.

Workup

  1. stirringThe reaction was stir for 1 h
  2. stirringThe reaction was stirred at −78° C. for 5 min
  3. customThe reaction was quenched with NH4Cl (saturated, 100 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. washThe combined organics were washed with brine (saturated, 200 mL)
  6. dry with materialdried with Na2SO4
  7. custompurified

Sources & evidence

ORD record
ord-70c099cb5821490d96182f2760252381
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

Loading…