Nitrogen → 4-(Pyridine-3-yloxy)ethynylbenzene

HRID 2035683Notes

Reaction equation

HRID 2035683 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:15]=[CH:14][C:11](C=O)=[CH:10][CH:9]=2)[CH:2]=1.[C:16](NC1C=CC(S(N=[N+]=[N-])(=O)=O)=CC=1)(=O)[CH3:17].C(=O)([O-])[O-].[K+].[K+].N#N>CC#N.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]#[C:15][C:14]2[CH:11]=[CH:10][CH:9]=[CH:17][CH:16]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 46774194-(Pyridin-3-yloxy)benzaldehydeHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 666830994-(Pyridine-3-yloxy)ethynylbenzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-(Pyridine-3-yloxy)benzaldehyde (0.500 g, 2.510 mmol), 4-acetamidobenzene sulfonyl azide (0.724 g, 3.01 mmol), dimethyl (2-oxopropyl) phosphonate (0.412 mL, 3.01 mmol), and potassium carbonate (1.041 g, 7.53 mmol) in MeCN (10.5 mL) and MeOH (2.1 mL) was heated to 40° C. for 16 h while under N2. The solvent was removed and residue was redissolved in EtOAc and washed with water (3×) and brine (1×). The organic phase was separated, dried with Na2SO4 and evaporated to afford an oil. This material was chromatographed on silica (0-80% EtOAc in hexanes) to yield 0.238 g as an oil.

Workup

  1. customThe solvent was removed
  2. dissolutionresidue was redissolved in EtOAc
  3. washwashed with water (3×) and brine (1×)
  4. customThe organic phase was separated
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. customto afford an oil
  8. customThis material was chromatographed on silica (0-80% EtOAc in hexanes)
  9. customto yield 0.238 g as an oil

Sources & evidence

ORD record
ord-1e4692f1880c4778892e8cd899fdbc62
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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