Hydrochloric Acid → 2-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazole-3-yl)benzo[b]furan

HRID 2183180Notes

Reaction equation

HRID 2183180 reaction equation
[O:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.C([Sn]([N:34]=[N+:35]=[N-:36])(CCCC)CCCC)CCC.O1CCOCC1.Cl>C1(C)C=CC=CC=1>[N:16]1[NH:34][N:35]=[N:36][C:15]=1[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:5]1[O:1][C:2]2[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 224798033-benzo[b]furan-2-yl-1H-indazole-5-carbonitrile

Product 1

HCID 224799072-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazole-3-yl)benzo[b]furanYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3-benzo[b]furan-2-yl-1H-indazole-5-carbonitrile (185 mg, 0.713 mmol) in toluene (10 mL) was added tributyl tin azide (0.780 mL). The solution was brought to 110° C. for 18 hours. The solution was cooled and toluene condensed to give an oil. Dioxane (3 mL) and 6 N HCl (3 mL) was added and the solution stirred for 3 hours at ambient temperature. The resulting precipitate was basified using 6 N HCl. The basic aqueous layer was washed with hexanes and ethyl acetate. The aqueous hydroxide solution was filtered through celite and acidified with 6 N HCl to pH 4. The resulting precipitate was filtered and dried to afford the title compound (25 mg, 12% yield). 1H NMR (DMSO-d6) δ 13.88 (s, 1H), 8.90 (s, 1H), 8.10 (d, 1H), 7.83 (d, 1H), 7.73 (d, 2H), 7.54 (s, 1H), 7.34 (m, 2H); ES-MS (m/z) 303 [M+1]+.

Workup

  1. temperatureThe solution was cooled
  2. customto give an oil
  3. washThe basic aqueous layer was washed with hexanes and ethyl acetate
  4. filtrationThe aqueous hydroxide solution was filtered through celite
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-c56d0f15575f4ba38121ffa2cb458ecb
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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