Isopropanol → HCID 58255767, compound

HRID 1695712Notes

Reaction equation

HRID 1695712 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.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH:31]=[CH:32][CH:33]=2)O1.C(=O)([O-])O.[Na+].C(O)(C)C>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].C(OCC)(=O)C.O>[N+:17]([C:4]1[C:5]2[C:9]([CH:10]=[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[CH:29]=3)[CH:3]=1)=[N:8][N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH:6]=2)([O-:19])=[O:18]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 218656112-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]oxaneHCID 582558186-Bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

Product 1

HCID 58255767HCID 58255767, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

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, 0.153 mmol), 2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}tetrahydro-2H-pyran (700 mg, 2.3 mmol), saturated sodium hydrogen carbonate (aq) (2 ml) and isopropyl alcohol (8 ml) were added to each of 5 microwave vessels. All 5 reactions were heated at 150° C. for 10 mins in a Biotage Initiator microwave. Reaction mixtures 1, 4, 5 were combined and water (250 ml) and ethyl acetate (250 ml) were added. The separated organic layer was washed with water followed by brine, then dried over sodium sulphate. The solvent was removed in vacuo and the residue was purified using silica gel chromatography, eluting with 10-35% ethyl acetate in cyclohexane. Appropriate fractions were combined and the solvent was removed in vacuo. This process was then repeated on combined reaction mixtures 2 and 3. Finally, the residues were combined to give the title compound, 1.06 g.

Workup

  1. customReaction
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified
  6. washeluting with 10-35% ethyl acetate in cyclohexane
  7. customthe solvent was removed in vacuo
  8. customreaction

Sources & evidence

ORD record
ord-4ca3d788a6164322a5f05bdd14685978
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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