Triphenylphosphine → HCID 89964226, compound

HRID 1846231Notes

Reaction equation

HRID 1846231 reaction equation
C=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]2[CH:16]=[CH:17][CH:18]=[N:19][C:3]1=2.BrC1C(N(CCCC=C)C(=O)[O:29]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:29]=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]2[CH:16]=[CH:17][CH:18]=[N:19][C:3]1=2

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 89964234HCID 89964234, compoundHCID 131732431HCID 131732431, compound

Product 1

HCID 89964226HCID 89964226, compound

Reagents, catalysts & solvents 5

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

Conditions

Temperature
110 °C

Procedure

tert-butyl 9-methylene-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine-5-carboxylate. To a solution of tert-butyl (2-bromopyridin-3-yl)(pent-4-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, dried over Na2SO4, and concentrated. The product 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 product thus obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-420a84676b5d47399ef8060f3b93ec9c
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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