Sodium Azide → HCID 178520466, compound

HRID 386466Notes

Reaction equation

HRID 386466 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[O:13][C:12]([C:14](=[O:31])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:19][CH:18]=3)=[N:11][CH:10]=2)[N:4]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+]>CC(O)C.O.[Br-].[Zn+2].[Br-]>[NH:32]1[C:1]([C:3]2[N:4]=[C:5]([C:9]3[O:13][C:12]([C:14](=[O:31])[CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:19][CH:18]=4)=[N:11][CH:10]=3)[CH:6]=[CH:7][CH:8]=2)=[N:2][N:34]=[N:33]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 24800521HCID 24800521, compound

Product 1

HCID 178520466HCID 178520466, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

2-Cyano-6-(2-(3-(4-(phenoxymethyl)phenyl)propanoyl)oxazol-5-yl)pyridine (98 mg, 0.24 mmol), sodium azide (31 mg, 0.48 mmol), and zinc bromide (27 mg, 0.12 mmol) were dissolved in i-PrOH/H2O (1:2, 2.1 mL) and warmed at reflux for 24 h. The reaction solution was allowed to cool to ambient temperature and was quenched with aqueous 1 N HCl. The solution was diluted with EtOAc and the organic phase was washed with saturated aqueous NaCl, dried over Na2SO4, and the solvent was removed in vacuo. The crude product was purified by tritration in 3% CH2Cl2/ether to provide 1-(5-(6-(1H-tetrazol-5-yl)pyridin-2-yl)oxazol-2-yl)-3-(4-(phenoxymethyl)phenyl)propan-1-one as a pale yellow solid (60 mg, 55%): NMR (DMSO-d6, 600 MHz) δ 8.25-8.24 (m, 3H), 8.08-8.05 (m, 1H), 7.38 (d, 2H, J=8.0 Hz), 7.31-7.27 (m, 4H), 6.99 (d, 2H, J=8.7 Hz), 6.92 (t, 1H, J=7.3 Hz), 3.47 (t, 2H, J=7.5 Hz), 3.02 (t, 2H, J=7.5 Hz); 13C NMR (DMSO-d6, 150 MHz) δ 207.8, 188.3, 159.7, 158.7, 153.0, 147.3, 141.6, 141.2, 136.2, 130.8, 129.7, 129.6, 129.2, 124.1, 123.3, 122.0, 116.1, 70.2, 32.0, 30.0; HR ESI-TOF m/z 453.1681 (M+H+, C25H20N6O3, requires 453.1670).

Workup

  1. temperaturewarmed
  2. temperatureat reflux for 24 h
  3. customwas quenched with aqueous 1 N HCl
  4. additionThe solution was diluted with EtOAc
  5. washthe organic phase was washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe crude product was purified by tritration in 3% CH2Cl2/ether

Sources & evidence

ORD record
ord-1013c47a830f49eeb606687bd6fc8685
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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