Isopropanol → 1-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79270Notes

Reaction equation

HRID 79270 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1.[B-](F)(F)(F)[CH:23]=[CH2:24].[K+].C(O)(C)C.C(N(CC)CC)C>O1CCCC1>[CH3:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:23]=[CH2:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 672597031-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazoleYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a reaction vial was added 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (216 mg, 0.548 mmol) and potassium trifluoro(vinyl)borate (156 mg, 1.64 mmol). Isopropanol (2 mL) and tetrahydrofuran (0.5 mL) were added. Argon was bubbled through the mixture for 20 minutes. Triethylamine (229 μL, 1.64 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (44.8 mg, 0.0548 mmol) were added. The vial was sealed and the mixture was heated at 90-100° C. for 3 hours. The mixture was allowed to cool and filtered through glass fiber filter paper, washing with ethyl acetate. The solution was concentrated under reduced pressure. The residue was dissolved in chloroform (30 mL) and washed with water (10 mL). The solution was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1-((6-methylpyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole as an oil (141 mg).

Workup

  1. customArgon was bubbled through the mixture for 20 minutes
  2. customThe vial was sealed
  3. temperatureto cool
  4. filtrationfiltered through glass fiber
  5. filtrationfilter paper
  6. washwashing with ethyl acetate
  7. concentrationThe solution was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in chloroform (30 mL)
  9. washwashed with water (10 mL)
  10. dry with materialThe solution was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d095b51903c94877b397a4f239969812
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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