Azido(trimethyl)stannane → HCID 178441500, compound

HRID 1742433Notes

Reaction equation

HRID 1742433 reaction equation
[CH2:1]([C:5]1[N:13]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26]#[N:27])=[CH:19]3)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[N:13]([C:14]2[C:15]3[C:20](=[CH:19][C:18]([C:24]4[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=4[C:26]4[NH:38][N:37]=[N:36][N:27]=4)=[CH:17][CH:16]=3)[CH:21]=[CH:22][CH:23]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 19008910HCID 19008910, compound

Product 1

HCID 178441500HCID 178441500, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 2-[5-(2-butyl-imidazo[4,5-b]pyridin-3-yl)-naphthalen-2-yl]-benzonitrile (85 mg, 0.21 mmol) and trimethyltin azide (108 mg, 0.50 mmol) in xylene (2.5 mL) was heated under reflux for 17 hours. The reaction mixture was cooled to 23° C. and the solvent was removed in vacuo. The crude residue was dissolved in EtOH (5 mL) and 2N NaOH (5 mL) was added. After 0.5 hour, the reaction mixture was concentrated in vacuo. The residue was dissolved in saturated aqueous NaCl (2 mL) and neutralized with concentrated HOAc. The aqueous solution was extracted with CHCl3 (3×10 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was azeotroped with heptane, diluted with EtOAc (1 mL) and hexanes (25 mL). The solid that precipitated was filtered and dried. 1H NMR (250 MHz, d6 -DMSO): d 8.13 (m, 3 H), 7.96 (s, 1 H), 7.65 (m, 6 H), 7.30 (m, 1 H), 7.12 (dd, 1 H), 6.86 (d, 1 H), 2.55 (m, 2 H), 1.63 (m, 2 H), 1.22 (m, 2 H), 0.74 (t, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude residue was dissolved in EtOH (5 mL)
  5. addition2N NaOH (5 mL) was added
  6. concentrationthe reaction mixture was concentrated in vacuo
  7. dissolutionThe residue was dissolved in saturated aqueous NaCl (2 mL) and neutralized with concentrated HOAc
  8. extractionThe aqueous solution was extracted with CHCl3 (3×10 mL)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe residue was azeotroped with heptane
  12. additiondiluted with EtOAc (1 mL) and hexanes (25 mL)
  13. customThe solid that precipitated
  14. filtrationwas filtered
  15. customdried

Sources & evidence

ORD record
ord-9f3e1f229fd849659f012e5d7309c5aa
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

Loading…