Cesium carbonate → HCID 117643582, compound

HRID 2171238Notes

Reaction equation

HRID 2171238 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.I[C:55]1[C:63]2[C:58](=[CH:59][CH:60]=[C:61]([N+:64]([O-:66])=[O:65])[CH:62]=2)[N:57]([CH3:67])[N:56]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O1CCOCC1>[CH3:67][N:57]1[C:58]2[C:63](=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[CH:60][CH:59]=2)[C:55]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:56]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 567738423-Iodo-1-methyl-5-nitro-1H-indazole

Product 1

HCID 117643582HCID 117643582, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Pyrrolidine (90 mg), cesium carbonate (500 mg), Pd2(dba)3 (46 mg), and Xantphos (58 mg) were added to a dioxane solution (4 ml) containing 3-iodo-1-methyl-5-nitro-1H-indazole (303 mg) obtained in the 1st step, followed by microwave irradiation (Initiator™, 160° C., 15 minutes, 2.45 GHz, 0-240 W). Then, ethyl acetate was added to the obtained residue, insoluble matter was removed by filtration, and the solvent was distilled away under reduced pressure. 1-Methyl-5-nitro-3-(pyrrolidine-1-yl)-1H-indazole (50 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. customfollowed by microwave irradiation (Initiator™, 160° C., 15 minutes, 2.45 GHz, 0-240 W)
  3. customwas removed by filtration
  4. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-2531a25d10764633a8e693522e28bd8c
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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