Tributyltin azide → HCID 178419934, compound

HRID 1349671Notes

Reaction equation

HRID 1349671 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][N:12]=1.[N:22]([Sn](CCCC)(CCCC)CCCC)=[N+:23]=[N-:24]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[NH:24][N:23]=[N:22][N:21]=3)[CH:18]=2)[NH:13][N:12]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 22479687HCID 22479687, compound

Product 1

HCID 178419934HCID 178419934, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(2-naphthyl)-1H-indazole-5-carbonitrile (105 mg, 0.390 mmol), azidotributyltin (Bu3SnN3, 710 mg, 2.14 mmol, 5.49 equiv.), and 4.1 mL toluene was refluxed for 49.5 h and concentrated to an oil. The oil was stirred in 31 mL dioxane and 31 mL 6.0 N aq HCl at room temperature for 4 h. The mixture was partitioned between 6.0 N aq. NaOH and hexanes, and the layers separated. The aqueous layer was extracted with hexanes, and 2×EtOAc, and then filtered. The aqueous layer was acidified to pH ca. 4.0 with 6.0 N aq. HCl. The resulting precipitate was either collected by filtration and dried in a vacuum oven, or extracted with EtOAc, dried (Na2SO4), filtered and concentrated to afford the title compound (78.4 mg, 64.3% yield): 1H NMR (DMSO-d6) δ 13.70 (s, 1H), 8.92 (s, 1H), 8.60 (s, 1H), 8.17 (d, 1H), 8.15–8.00 (m, 3H), 7.94 (d, 1H), 7.85 (d, 1H), 7.63–7.58 (m, 2H); ES-MS (m/z) 313 [M+1]+.

Workup

  1. temperaturewas refluxed for 49.5 h
  2. concentrationconcentrated to an oil
  3. customThe mixture was partitioned between 6.0 N aq. NaOH and hexanes
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with hexanes, and 2×EtOAc
  6. filtrationfiltered
  7. filtrationThe resulting precipitate was either collected by filtration
  8. customdried in a vacuum oven
  9. extractionextracted with EtOAc
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-507f515cb37c45e986455e7497d67424
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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