N,N-Dimethylglycine → HCID 24826366, compound

HRID 1988685Notes

Reaction equation

HRID 1988685 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.Br[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:3]([C:2]([F:1])([F:12])[F:13])=[N:4]2)=[CH:16][CH:17]=1)[CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 673N,N-Dimethylglycine2×HCID 11430Potassium CarbonateHCID 27341981-bromo-4-propoxybenzeneHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 24826366HCID 24826366, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (152 mg, 0.8 mmol), 1-bromo-4-(propyloxy)benzene (177 mg, 0.8 mmol), N,N-dimethylglycine (16 mg, 0.16 mmol), copper (I) iodide (16 mg, 0.08 mmol), potassium carbonate (235 mg, 1.7 mmol) in dimethylsulfoxide (3 ml) was heated in a microwave reactor at 180° C. for a total of 50 minutes. Fresh N,N-dimethylglycine (16 mg, 0.16 mmol) and copper (I) iodide (16 mg, 0.08 mmol) was added and heating continued at 180° C. for a further 30 minutes. The reaction mixture was then filtered through a 5 g sep-pack column with 40 ml 1:1 ethyl acetate in petroleum ether. The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was retained and washed with brine (2×10 ml), then dried over sodium sulphate. The solvent was removed by rotary evaporation and the sample purified by MDAP. The relevant fractions were combined and the solvent removed by rotary evaporation to give the title compound (23 mg, 9%).

Workup

  1. temperatureheating
  2. filtrationThe reaction mixture was then filtered through a 5 g sep-pack column with 40 ml 1:1 ethyl acetate in petroleum ether
  3. customThe solvent was removed by rotary evaporation
  4. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  5. washwashed with brine (2×10 ml)
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was removed by rotary evaporation
  8. customthe sample purified by MDAP
  9. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-57298ded2a804c27a7aca50902d586ac
Source dataset
uspto-grants-2010_01
Patent number
US07642256B2

Reaction notes

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