Tributylvinyltin → HCID 21931759, compound

HRID 1244043Notes

Reaction equation

HRID 1244043 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1Br.[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC>CN(P(N(C)C)(N(C)C)=O)C.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[CH:17]=[CH2:18]

Participants

7

Reactant 2

HCID 81998TributylvinyltinHCID 21931760HCID 21931760, compound

Product 1

HCID 21931759HCID 21931759, compoundYield 735.5%

Reagents, catalysts & solvents 4

HCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 138 mg (0.048 mmol) 5-methoxy-6-bromo-1,3,3-trimethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one, 138 mg (0.48 mmol) of tri-n-butyl-vinyltin and 15 mg of bis(triphenylphosphine-palladium(II) chloride in 1 ml of HMPA was heated under nitrogen to 65° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with water and ethyl acetate. The ethyl acetate solution was washed with water several times. To this ethyl acetate solution was added 1 ml of saturated KF, and the mixture filtered. The filtrate was dried (Na2SO4), evaporated, and the residue chromatographed on silica using 1:1 ethyl acetate/hexanes as the elutant. Appropriate fractions were combined and evaporated to afford 82 mg of 5-methoxy-1,3,3-trimethyl-6-vinyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one. 1H NMR (CDCl3) δ 6.90 (d,d 1H), 5.75 (d, 1H), 5.30 (d, 1H), 3.95 (s, 3H), 3.20 (s, 3H), 1.40 (s, 6H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe ethyl acetate solution was washed with water several times
  3. additionTo this ethyl acetate solution was added 1 ml of saturated KF
  4. filtrationthe mixture filtered
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. customevaporated
  7. customthe residue chromatographed on silica using 1:1 ethyl acetate/hexanes as the elutant
  8. customevaporated

Sources & evidence

ORD record
ord-8a6866877802461da5457eb3ef7458e2
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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