Phenylacetylene → HCID 68866633, compound

HRID 729988Notes

Reaction equation

HRID 729988 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][NH:8][C:6]1[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=[C:2]([C:24]#[C:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 611678716-Chloro-N-(2,2-dimethylpropyl)-3-nitro-2-pyridinamine

Product 1

HCID 68866633HCID 68866633, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
75 °C

Procedure

Dissolve (6-chloro-3-nitropyridin-2-yl)-(2,2-dimethylpropyl)amine (7.3 g, 30.0 mmol), phenylacetylene (5.0 mL, 45 mmol) and triphenylphosphine (1.5 mmol, 0.39 g) in triethylamine (10 mL/g) in an oven-dried round bottom flask is flushed with nitrogen and evacuated three times. Add Pd(OAc)2 (0.10 g, 0.45 mmol) and the nitrogen flush/evacuation cycle is repeated (3×). Heat at 70-80° C. with stirring under nitrogen for 1-3 h, then cool at RT for 2 h. Concentrate and partition between water (25 mL) and EtOAc (150 mL). Separate the organic layer and wash with water (4×25 mL), saturated aqueous NaCl (25 mL), dry with MgSO4, filter, and concentrate. Purify the crude solid by recrystallization from EtOAc/hexanes to give the title product as a bright orange solid (6.5 g, 21.2 mmol, 71%).

Workup

  1. customis flushed with nitrogen
  2. customevacuated three times
  3. temperaturecool at RT for 2 h
  4. concentrationConcentrate
  5. custompartition between water (25 mL) and EtOAc (150 mL)
  6. customSeparate the organic layer
  7. washwash with water (4×25 mL), saturated aqueous NaCl (25 mL)
  8. dry with materialdry with MgSO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify the crude solid
  12. customby recrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-f225dd7f69f74113b41b5811612106ab
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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