Water → HCID 67047975, compound

HRID 2362428Notes

Reaction equation

HRID 2362428 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1)=[N+]=[N-].CP(C)C.O>O1CCCC1>[C:13]1([C:12]#[C:11][C:9]2[CH:10]=[C:5]([CH2:4][NH2:1])[CH:6]=[N:7][CH:8]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86673448HCID 86673448, compound

Product 1

HCID 67047975HCID 67047975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(azidomethyl)-5-(phenylethynyl)pyridine (7.8 g, 33.3 mmol) in tetrahydrofuran (101 mL) at 0° C. was added trimethylphosphine (1M in tetrahydrofuran, 49.9 mL, 49.9 mmol). After evolution of nitrogen had slowed, the ice bath was removed and stirring continued for 1 h. To this was added water (6.0 mL, 333 mmol) and the mixture stirred at room temperature for 2 h. The reaction was concentrated, dissolved in ether, washed with water (5×), then brine, dried over potassium carbonate, filtered, and concentrated to give 5.96 g (77%) as a faint yellow solid which was used without purification. 1H NMR (CDCl3) δ: 8.67 (d, J=1.8 Hz, 1H), 8.52 (d, J=2.1 Hz, 1H), 7.85 (t, J=2.0 Hz, 1H), 7.53-7.61 (m, 2H), 7.35-7.44 (m, 3H), 3.95 (s, 2H), 1.45 (d, J=5.2 Hz, 2H)1H NMR (CDCl3) δ: 8.67 (d, J=1.8 Hz, 1H), 8.52 (d, J=2.1 Hz, 1H), 7.85 (t, J=2.0 Hz, 1H), 7.53-7.61 (m, 2H), 7.35-7.44 (m, 3H), 3.95 (s, 2H), 1.45 (d, J=5.2 Hz, 2H). 13C NMR (CDCl3) δ: 150.8, 147.9, 137.8, 137.4, 131.8, 128.9, 128.6, 122.7, 120.3, 92.7, 86.1, 43.7. Mass spec.: 209.1 (MH)+.

Workup

  1. customthe ice bath was removed
  2. stirringthe mixture stirred at room temperature for 2 h
  3. concentrationThe reaction was concentrated
  4. dissolutiondissolved in ether
  5. washwashed with water (5×)
  6. dry with materialbrine, dried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give 5.96 g (77%) as a faint yellow solid which
  10. customwas used without purification

Sources & evidence

ORD record
ord-d978c1c7e23041a1b604dc1dd6ff7a6f
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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