Water → 2-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylethanamine

HRID 246673Notes

Reaction equation

HRID 246673 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][N:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[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][N:16]([CH3:18])[CH3:17])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178422878HCID 178422878, compound

Product 1

HCID 712800902-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylethanamineYield 151.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-iodo-6-methyl-1H-indazole (516 mg, 2 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (346 mg, 2.4 mmol) and potassium carbonate (828 mg, 6 mmol) in 20 mL of DMF was heated to 80 degree overnight. After cooling to room temperature, water (50 mL) was added, product extracted with dichloromethane (3×50 mL), combined organics were dried with sodium sulfate, and concentrated to give 2-(3-iodo-6-methyl-1H-indazol-1-yl)-N,N-dimethylethanamine (1 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.33 (d, 1H, J=8.1 Hz), 7.15 (s, 1H), 7.03 (d, 1H, J=0.6 Hz), 4.47 (t, 2H, J=7.2 Hz), 2.81 (t, 2H, J=7.2 Hz), 2.51 (s, 3H), 2.34 (m, 6H).

Workup

  1. temperaturewas heated to 80 degree overnight
  2. extractionproduct extracted with dichloromethane (3×50 mL)
  3. dry with materialcombined organics were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1581bc42fc2b4cf18adf71249009b114
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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