1-Methyl-3-aminopyrazole → HCID 25261180, compound

HRID 1966230Notes

Reaction equation

HRID 1966230 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.[CH3:10][N:11]1[CH:15]=[CH:14][C:13]([NH2:16])=[N:12]1>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1N(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:16][C:13]2[CH:14]=[CH:15][N:11]([CH3:10])[N:12]=2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 111481512-Bromo-5-methoxypyridine

Product 1

HCID 25261180HCID 25261180, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178482626HCID 178482626, compoundCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

2-Bromo-5-methoxy-pyridine (0.97 mmol), sodium-tert.-butylate (1.5 eq.), and 1-methyl-1H-pyrazole-3-amine (1.3 eq.) are dissolved in degassed dioxane (2 ml) and heated to 80° C. Chloro-(di-2-norbornylphosphino)(2-dimethylaminoferrocene-1-yl)palladium (II) (5 mg) in degassed dioxane (1 ml) is added and the reaction is heated for 20 hours at 110° C. The reaction is quenched with ethylacetate/methanol (30 ml, 9:1) and filtrated over celite. The solvent of the filtrate is removed in vacuo. (5-Methoxy-pyridine-2-yl)-(1-methyl-1H-pyrazole-3-yl)-amine (“A24”) is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TFA) as colorless powder in a yield of 55%; HPLC (method C): 1.09 min; LC-MS (method A): 0.73 min, 205.0 (M+H+);

Workup

  1. temperaturethe reaction is heated for 20 hours at 110° C
  2. customThe reaction is quenched with ethylacetate/methanol (30 ml, 9:1)
  3. filtrationfiltrated over celite
  4. customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record
ord-a4f15915cb50453781233f67e39f75e1
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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