Dodecane → 3-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamine

HRID 2266687Notes

Reaction equation

HRID 2266687 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:20])=[N:15][CH:16]=[C:17](I)[CH:18]=1)[CH3:11].[CH3:21][C:22]1[CH:26]=[CH:25][NH:24][N:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCCCCCCCCCCC.C1(N)(N)CCCCC1>CS(C)=O.[Cu](I)I>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:20])=[N:15][CH:16]=[C:17]([N:24]2[CH:25]=[CH:26][C:22]([CH3:21])=[N:23]2)[CH:18]=1)[CH3:11]

Participants

8

Reactant 5

HCID 8182DodecaneHCID 62657Potassium Phosphate, TribasicHCID 17842493Cyclohexane-1,1-diamineHCID 211113953-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-iodopyridin-2-amineHCID 178428694HCID 178428694, compound

Product 1

HCID 115453903-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamineYield 34.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-iodo-pyridin-2-ylamine (100 mg, 0.23 mmol) and 3-methyl-1H-pyrazole (59 mg, 0.70 mmol) in DMSO (1 mL was added K3PO4 (101 mg, 0.47 mmol), dodecane (0.015 mL, 0.05 mmol), cyclohexanediamine (0.009 mL, 0.07 mmol) and copper iodide (CuI) (14 mg, 0.07 mmol). The solution was bubbled with nitrogen for 5 minutes, then radiated with microwave at 150° C. for 2 hours, LCMS checked that the reaction was completed, the mixture was purified by prep-HPLC to leave 3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(3-methyl-pyrazol-1-yl)-pyridin-2-ylamine (30 mg), yield 34.2%

Workup

  1. customThe solution was bubbled with nitrogen for 5 minutes
  2. customthe mixture was purified by prep-HPLC

Sources & evidence

ORD record
ord-b200e6f1b0964a1685216234a2dfd2e5
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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