N,N-Dimethylglycine → HCID 24826367, compound

HRID 230697Notes

Reaction equation

HRID 230697 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=2)=[CH:23][CH:22]=1.CN(C)CC(O)=O>CS(C)=O.[Cu]I>[CH3:32][N:30]1[CH:31]=[C:27]([C:24]2[CH:23]=[CH:22][C:21]([N:5]3[C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=4[C:3]([C:2]([F:1])([F:12])[F:13])=[N:4]3)=[CH:26][CH:25]=2)[N:28]=[CH:29]1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 11430Potassium CarbonateHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleHCID 532492914-(4-Bromophenyl)-1-methyl-1H-imidazole

Product 1

HCID 24826367HCID 24826367, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of copper (I) iodide (10 mol %, 5 mg, 0.02 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (50 mg, 0.26 mmol), potassium carbonate (73 mg, 0.52 mmol) in DMSO (2 ml) was stirred for 1 min, then 4-(4-bromophenyl)-1-methyl-1H-imidazole (62 mg, 0.26 mmol) (WO91/09855) and N,N-dimethylglycine (20 mol %, 5.4 mg) were then successively added. The reaction tube was quickly sealed and the contents were heated in a microwave reactor at 180° C. for 40 mins. The reaction mixture was partitioned between ethyl acetate and water, dried with sodium sulphate and solvent was removed by rotary evaporation and the sample purified by MDAP. The solvent was removed by rotary evaporation to give the title compound as a solid (15 mg, 16%).

Workup

  1. customThe reaction tube was quickly sealed
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialdried with sodium sulphate and solvent
  4. customwas removed by rotary evaporation
  5. customthe sample purified by MDAP
  6. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-c92c284de57b4c9cbc646daa5136f2b1
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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