Dimethylformamide → 3-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine

HRID 246677Notes

Reaction equation

HRID 246677 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.Cl.Cl[CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 178422878HCID 178422878, compound

Product 1

HCID 712802213-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amineYield 50.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-iodo-6-methyl-1H-indazole (2.58 g, 10 mmol), 3-chloro-N,N-dimethylpropan-1-amine hydrochloride (2.37 g, 15 mmol) and potassium carbonate (4.14 g, 30 mmol) in 50 ml, of DMF was heated to 85° C. for 3 hours. After cooling to room temperature, 100 mL of water was added and the mixture was extracted with ethyl acetate (4×100 mL). Then the combined organic phases were added with 20 mL of 6N HCl, and the solution was extracted with dichloromethane (4×50 mL). The combined organic phases were dried with sodium sulfate, concentrated to give 3-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.74 g, 50.6%). LCMS: (M+H)+=344; 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 1H, J=8.4 Hz), 7.21 (s, 1H), 7.03 (d, 1H, J=8.4 Hz), 4.43 (t, 2H, J=6.6 Hz), 2.51 (s, 3H), 2.27-2.23 (m, 8H), 2.09-2.07 (m, 2H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×100 mL)
  2. additionThen the combined organic phases were added with 20 mL of 6N HCl
  3. extractionthe solution was extracted with dichloromethane (4×50 mL)
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85ad9f8fe99d465cb396467d17a0b385
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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