Tris(1,1-dimethylethyl)phosphine → HCID 59332876, compound

HRID 1879982Notes

Reaction equation

HRID 1879982 reaction equation
CC(C)([O-])C.[K+].Br[C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=[CH:10][N:9]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1COCC1>[N:9]1[C:8]2[NH:18][CH2:17][CH2:16][CH2:15][O:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23665647Potassium tert-butoxideHCID 59332899HCID 59332899, compound

Product 1

HCID 59332876HCID 59332876, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Potassium tert-butoxide (18 mL, 18 mmol) was added to a THF (120 mL) solution of 3-(2-bromo-pyridin-3-yloxy)-propylamine (2.75 g, 11.9 mmol). The solution was purged with an Ar stream for 10 min, bis(dibenzylideneacetone)palladium (342 mg, 0.6 mmol) and tri-tert-butylphosphine (2.1 mL, 0.7 mmol, 10% in hexane) were added and the mixture was stirred at 60° C. for 5 h. The solvent was evaporated, the residue was dissolved in CH2Cl2. This solution was washed with water, dried and evaporated. Chromatographic purification (silica, 0-2% MeOH in CH2Cl2) afforded 0.75 g (42%) of the title compound. 1H NMR (300 MHz, DMSO-d6, 8): 7.70 (dd, J=4.8, 1.4 Hz, 1H), 7.09 (dd, J=7.7, 1.4 Hz, 1H), 6.60 (dd, J=4.8, 7.7 Hz, 1H), 6.02 (s, br, 1H), 4.06 (t, J=5.5 Hz, 2H), 3.21 (m, 2H), 1.90 (m, 2H).

Workup

  1. customThe solution was purged with an Ar stream for 10 min
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washThis solution was washed with water
  5. customdried
  6. customevaporated
  7. customChromatographic purification (silica, 0-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c8252d6ef1ed495eab0b4ff0aa7e74e6
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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