Potassium Iodide → HCID 58598141, compound

HRID 389715Notes

Reaction equation

HRID 389715 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CC#N>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 58598141HCID 58598141, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2-(dimethylamino)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine was prepared by heating 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (0.219 g, 1 mmol), potassium iodide (0.006 g, 0.03 mmol), potassium carbonate (0.060 g, 0.4 mmol) and 2-dimethylaminoethyl chloride hydrochloride (0.043 g, 0.3 mmol) in MeCN (2 ml) to 110° C. by microwave irradiation for 10 minutes. The crude reaction was purified by preparative HPLC to give the desired compound as a white solid, (0.025 g, 0.086 mmol). LCMS (3) 2.12 min; m/z (ES+) 291

Workup

  1. customby microwave irradiation for 10 minutes
  2. customThe crude reaction
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-56ac13bf738f4173a68917ac59c531e1
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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