Sodium Carbonate → 5-[3-Chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamine

HRID 83558Notes

Reaction equation

HRID 83558 reaction equation
I[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([NH2:13])[CH:3]=1.[Cl:14][C:15]1[CH:16]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:18]=[C:19]([CH2:21][O:22][C:23]([CH3:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])[CH:20]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:5]=[C:4]([NH2:13])[CH:3]=2)[CH:18]=[C:19]([CH2:21][O:22][C:23]([CH3:29])([CH3:28])[C:24]([F:25])([F:26])[F:27])[CH:20]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 712877992-[3-Chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 86680350HCID 86680350, compound

Product 1

HCID 866803815-[3-Chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-1-phenyl-1H-pyrazol-3-ylamineYield 107.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under argon atmosphere, to a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (40 mg) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (1.0 ml) were sequentially added 2-[3-chloro-5-(2,2,2-trifluoro-1,1-dimethylethoxymethyl)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (64 mg), palladium (II) acetate (3 mg), tricyclohexylphosphine (8 mg) and a 2M aqueous solution of sodium carbonate (0.5 ml) at room temperature, and the mixture was stirred at 100° C. for 13 hours. This reaction mixture was cooled to room temperature, and then purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate 3/2 to 1/1) to give the titled compound (62 mg).

Workup

  1. custompurified by silica gel column chromatography (eluent: n-hexane/ethyl acetate 3/2 to 1/1)

Sources & evidence

ORD record
ord-95cad68992ae4fc3ba1bdddd08dc1887
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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