Potassium Phosphate, Tribasic → HCID 67778662, compound

HRID 1026231Notes

Reaction equation

HRID 1026231 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[C:13]3[C:9]([CH:10]=[N:11][NH:12]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CNC1CCCCC1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O.[Cu]I.C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:11]2[CH:10]=[C:9]3[C:13]([CH:14]=[C:6]([O:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH:7]=[CH:8]3)=[N:12]2)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 67778171HCID 67778171, compound

Product 1

HCID 67778662HCID 67778662, compoundYield 100.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-(cyclopropylmethoxy)-1H-indazole (376 mg), 1-(benzyloxy)-4-bromobenzene (632 mg), copper(I) iodide (38.1 mg), (1RS,2RS)—N,N′-dimethylcyclohexane-1,2-diamine (114 mg), tripotassium phosphate (892 mg) and toluene (2 mL) was stirred under an argon atmosphere at 110° C. overnight. The reaction mixture was diluted with ethyl acetate and water, and filtered through celite. The organic layer separated from the obtained filtrate was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give a mixture (741 mg) of the title compound and 1-[4-(benzyloxy)phenyl]-6-(cyclopropylmethoxy)-1H-indazole.

Workup

  1. filtrationfiltered through celite
  2. customThe organic layer separated from the obtained filtrate
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-770a70542ebb4890a2acc1e149615cea
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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