Triphenylphosphine → HCID 89964282, compound

HRID 1846235Notes

Reaction equation

HRID 1846235 reaction equation
C=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.C(N(C1C(Br)=NC=CC=1)C(=O)[O:23]C(C)(C)C)C=C.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:23]=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 68559071HCID 68559071, compoundHCID 89964062HCID 89964062, compound

Product 1

HCID 89964282HCID 89964282, compound

Reagents, catalysts & solvents 5

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

Conditions

Temperature
110 °C

Procedure

tert-butyl 3-methylene-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate. To a solution of tert-butyl allyl(2-bromopyridin-3-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 product 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 product that may be thus obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-9c565f3a3a3646329a5e7a66f2aef4c7
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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