Triphenylphosphine → HCID 89964768, compound

HRID 1846224Notes

Reaction equation

HRID 1846224 reaction equation
C=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4][CH2:3]1.BrC1C(N(CCC=C)C(=O)[O:28]C(C)(C)C)=CC=CN=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+]>CN(C=O)C.O.[Cl-].C([N+](CC)(CC)CC)C.CCOC(C)=O.C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Pd+2]>[O:28]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4][CH2:3]1

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 89964818HCID 89964818, compoundHCID 131732430HCID 131732430, compound

Product 1

HCID 89964768HCID 89964768, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

tert-butyl 4-methylene-3,4-dihydro-1,5-naphthyridine-1(2H)-carboxylate. To a solution of tert-butyl (2-bromopyridin-3-yl)(but-3-en-1-yl)carbamate (1 eq.) in DMF (0.2 M), PPh3 (0.25 eq.), Pd(OAc)2 (0.1 eq), and KOAc (5 eq.), is added, under an argon atmosphere, tetraethyl ammonium chloride hydrate (2 eq.). The flask is purged with argon for 15 min, and the resulting reaction mixture is stirred at 110° C. for 16 h. The reaction progress is monitored by TLC. The reaction mixture is diluted with EtOAc and saturated NaHCO3 solution. The organic layer is separated and dried over Na2SO4, and concentrated. The compound that may be thus obtained is purified by column chromatography to afford the title compound.

Workup

  1. customThe flask is purged with argon for 15 min
  2. customthe resulting reaction mixture
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe compound that may be thus obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-a9eb07f892124ae7af0839775f8751fc
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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