Potassium Carbonate → HCID 66747101, compound

HRID 1467121Notes

Reaction equation

HRID 1467121 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[C:3]=1[C:4]#[N:5].[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[CH:18]=2)[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 98130382-Amino-6-bromobenzonitrile

Product 1

HCID 66747101HCID 66747101, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-6-bromobenzonitrile (195 mg, 1.0 mmol) and (3-methoxyphenyl)boronic acid (300 mg, 2 mmol) in dioxane (2 mL) was added aqueous potassium carbonate (2.0 mmol, 0.7 mL). The reaction solution was degassed by bubbling N2 for 2 minutes. Palladium tetrakistriphenylphosphine (5% mol) was added to the reaction mixture and the reaction vessel was placed in a microwave reactor and irradiated at 165° C. for 20 minutes. The precipitate was removed by filtration and the filtrate concentrated. The residue was purified by HPLC (acetonitrile/water; 10-90% gradient, 25 minutes) to give the title compound as an off-white solid (180 mg, 80%). MS 225 (MH+).

Workup

  1. customThe reaction solution was degassed
  2. customby bubbling N2 for 2 minutes
  3. additionPalladium tetrakistriphenylphosphine (5% mol) was added to the reaction mixture
  4. customthe reaction vessel was placed in a microwave reactor
  5. customirradiated at 165° C. for 20 minutes
  6. customThe precipitate was removed by filtration
  7. concentrationthe filtrate concentrated
  8. customThe residue was purified by HPLC (acetonitrile/water; 10-90% gradient, 25 minutes)

Sources & evidence

ORD record
ord-e1a2be627f344ccba5a86be7e3facdfd
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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