Sodium Carbonate → HCID 90308830, compound

HRID 2283691Notes

Reaction equation

HRID 2283691 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[C:25]2[C:21](=[CH:22][N:23]([CH3:26])[N:24]=2)[CH:20]=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1>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].O1CCOCC1>[CH3:26][N:23]1[CH:22]=[C:21]2[C:25]([C:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[CH:20]2)=[N:24]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 90308679HCID 90308679, compound

Product 1

HCID 90308830HCID 90308830, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Phenylboronic acid (244 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1, 40 mg), dioxane (4 mL), a 2 M aqueous sodium carbonate solution (1 mL), and the reaction solution were added to 7-bromo-2-methyl-5-nitro-2H-indazole obtained in the above-described Step 1 (256 mg). The reaction solution was allowed to react in a microwave reactor at 130° C. for 1 hour. The solvent was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 2-methyl-5-nitro-7-phenyl-2H-indazole.

Workup

  1. customobtained in the above-described Step 1 (256 mg)
  2. customto react in a microwave reactor at 130° C. for 1 hour
  3. customThe solvent was evaporated under vacuum
  4. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4d61d38b14f6474382b98ad6071e0fdc
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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