Tributyltin azide → 1-(5-(2H-1,2,3,4-Tetrazol-5-Yl)(1H-Indazol-3-Yl))-2-Methoxybenzene

HRID 2183164Notes

Reaction equation

HRID 2183164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[NH:11][N:10]=1.[N:20]([Sn](CCCC)(CCCC)CCCC)=[N+:21]=[N-:22]>C1(C)C=CC=CC=1>[N:19]1[NH:20][N:21]=[N:22][C:18]=1[C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 224800393-(2-methoxyphenyl)-1H-indazole-5-carbonitrile

Product 1

HCID 224800881-(5-(2H-1,2,3,4-Tetrazol-5-Yl)(1H-Indazol-3-Yl))-2-Methoxybenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(2-methoxyphenyl)-1H-indazole-5-carbonitrile in toluene (20 mL) was added azidotributyl tin (0.716 g, 0.591 mL, 2.156 mmol). The reaction mixture was heated to reflux temperature for 18 hours. The solvent was removed under reduced pressure with no heat. The resulting oil was dissolved in tetrahydrofuran (2 mL) and toluene was added (20 mL). Hydrogen chloride was bubbled through the solution for 15 min, which resulted in the precipitation of a white solid. The product was collected by filtration after cooling to 0° C. and was washed with 5 mL portions of toluene. The impure solid was dissolved in 5 mL of aqueous sodium hydroxide (2.0 N) and the aqueous phase was washed with ethyl acetate. The product was precipitated out of the aqueous phase by bubbling hydrogen chloride gas. The solid was collected by filtration and washed with small portions of water. The product was isolated as an off-white solid after drying in a vacuum oven (0.110 g, 0.377 mmol, 20% over 2 steps): 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 8.4 (s, 1H), 8.0 (d, 1H), 7.7 (d, 1H), 7.5 (d, 1H), 7.4 (t, 1H), 7.2 (d, 1H), 7.1 (t, 1H), 3.8 (s, 3H); ES-MS (m/z) 293 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 18 hours
  3. customThe solvent was removed under reduced pressure with no heat
  4. dissolutionThe resulting oil was dissolved in tetrahydrofuran (2 mL)
  5. additiontoluene was added (20 mL)
  6. customHydrogen chloride was bubbled through the solution for 15 min
  7. customwhich resulted in the precipitation of a white solid
  8. filtrationThe product was collected by filtration
  9. washwas washed with 5 mL portions of toluene
  10. dissolutionThe impure solid was dissolved in 5 mL of aqueous sodium hydroxide (2.0 N)
  11. washthe aqueous phase was washed with ethyl acetate
  12. customThe product was precipitated out of the aqueous phase
  13. customby bubbling hydrogen chloride gas
  14. filtrationThe solid was collected by filtration
  15. washwashed with small portions of water
  16. customThe product was isolated as an off-white solid
  17. customafter drying in a vacuum oven (0.110 g, 0.377 mmol, 20% over 2 steps)

Sources & evidence

ORD record
ord-64cf3a9223f4414fa73d4534031d0845
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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