Sodium Carbonate → HCID 58255828, compound

HRID 1695716Notes

Reaction equation

HRID 1695716 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2.[CH3:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]3[C:9]([CH:10]=2)=[N:8][N:7]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:6]=3)[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27339503-Tolylboronic acidHCID 582558186-Bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

Product 1

HCID 58255828HCID 58255828, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

6-Bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (500 mg, 1.53 mmol), Pd(dppf)Cl2 (125 mg, 0.15 mmol), (3-methylphenyl)boronic acid (313 mg, 2.3 mmol), 1,4-dioxane (5 ml), 2 M sodium carbonate (aq) (2.3 ml) and water (5 ml) were combined and heated in a Biotage microwave at 150° C. for 30 mins. The crude reaction was combined with a separate reaction carried out at 1/10th scale. The combined reactions were partitioned between water (100 ml) and ethyl acetate (100 ml), filtered and the separated organic layer was washed several times with water, followed by brine, before being dried over magnesium sulphate and the solvent removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-25% ethyl acetate in cyclohexane, to give the title compound, 422 mg.

Workup

  1. customThe crude reaction
  2. customwas combined with a separate reaction
  3. customThe combined reactions were partitioned between water (100 ml) and ethyl acetate (100 ml)
  4. filtrationfiltered
  5. washthe separated organic layer was washed several times with water
  6. dry with materialbefore being dried over magnesium sulphate
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 0-25% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-daafcdc7c9f24b33a3274828b7cc5797
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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