Dibutyltin oxide → 5-((E)-1-(4-((E)-2-(2H-Tetrazol-5-yl)vinyl)phenyl)-2-phenylbut-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1057207Notes

Reaction equation

HRID 1057207 reaction equation
[C:1]1(/[C:7](/[CH2:34][CH3:35])=[C:8](\[C:24]2[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]#[N:33])=[CH:26][CH:25]=2)/[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N:40]=[N+:41]=[N-:42])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[N:33]1[NH:40][N:41]=[N:42][C:32]=1/[CH:31]=[CH:30]/[C:27]1[CH:26]=[CH:25][C:24](/[C:8](/[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:13]=[CH:12]3)=[C:7](\[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)/[CH2:34][CH3:35])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 66802201(E)-3-(4-((E)-2-Phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylonitrile

Product 1

HCID 668023615-((E)-1-(4-((E)-2-(2H-Tetrazol-5-yl)vinyl)phenyl)-2-phenylbut-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 40 mL vial equipped with a magnetic stir bar was charged with (E)-3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylonitrile (100 mg, 0.22 mmol), trimethylsilylazide (289 μL, 2.2 mmol), and di-n-butyltin oxide (11 mg, 0.04 mmol) in anhydrous toluene (2 mL). This mixture was degassed with 3 vacuum/N2 cycles, and then refluxed overnight. The reaction was poured onto silica and eluted with hexane (50 mL) and then 20% methanol in DCM (100 mL). The filtrate was concentrated to give the crude product that was purified on a silica gel column eluted with 0-15% methanol in DCM affording the title compound (49 mg, 45%). 1H NMR (DMSO-d6, 300 MHz): δ 8.13 (s, 1H), 7.74 (d, 1H), 7.66 (m, 1H), 7.49-7.36 (m, 3H), 7.29-7.13 (m, 7H), 6.91 (d, 2H), 5.87 (dd, 1H), 3.92-3.89 (m, 1H), 3.84-3.71 (m, 1H), 2.49-2.42 (m, 3H), 2.09-1.97 (m, 2H), 1.85-1.67 (m, 1H), 1.63-1.51 (m, 2H), 0.90 (t, 3H). LCMS: 503 (M+H)+.

Workup

  1. customA 40 mL vial equipped with a magnetic stir bar
  2. customThis mixture was degassed with 3 vacuum/N2 cycles
  3. temperaturerefluxed overnight
  4. additionThe reaction was poured onto silica
  5. washeluted with hexane (50 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-75c83b742f4a462494a6e2e8e54ebdb5
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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