Potassium Carbonate → N-(3-(4-Bromo-pyrazol-1-yl)-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 77883Notes

Reaction equation

HRID 77883 reaction equation
I[C:2]1[C:3]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:15][C:16]1[CH:17]=[N:18][NH:19][CH:20]=1.[C@@H]1(N)CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.C1(C)C=CC=CC=1>[Br:15][C:16]1[CH:17]=[N:18][N:19]([C:2]2[C:3]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 438061,2-Diaminocyclohexane, trans-HCID 10946636N-(3-Iodopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 59255076N-(3-(4-Bromo-pyrazol-1-yl)-pyridin-2-yl)-2,2-dimethyl-propionamideYield 53.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of N-(3-iodo-pyridin-2-yl)-2,2-dimethyl-propionamide (380 mg, 1.2 mmol) described in Manufacturing Example 39-1-2 and toluene (10 mL) were added 4-bromopyrazole (160 mg, 1.1 mmol), copper (I) iodide (11 mg, 0.056 mmol), trans-1,2-cyclohexanediamine (26 mg, 0.22 mmol) and potassium carbonate (340 mg, 2.5 mmol) at room temperature, which was stirred overnight at 110° C. The reaction mixture was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (190 mg, 52%).

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1)

Sources & evidence

ORD record
ord-46d5cd948674461d9956f6455fb5cacc
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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