Sodium Carbonate → HCID 23521687, compound

HRID 392462Notes

Reaction equation

HRID 392462 reaction equation
I[C:2]1[CH:3]=[C:4]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:3][C:2]=1[C:27]1[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 23521705HCID 23521705, compound

Product 1

HCID 23521687HCID 23521687, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(3-iodo-4-methylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (103 mg,0.247 mmol) and 4-cyanophenylboronic acid (55 mg, 0.371 mmol) in 4 ml of 1,4-dioxane stirring under nitrogen was treated with 2M sodium carbonate (0.37 mL, 0.741 mmol) and tetrakis(triphenylphosphine)palladium(0) (12.6 mg, 0.011 mmol). This was refluxed for three hours and then allowed to stir at room temperature for 16 hours. The reaction had not completed after this time so the reaction was treated with an additional 5.7 mg(0.005 mmol) of tetrakis(triphenylphosphine)palladium(0) and refluxed for two hours. The reaction was then cooled to room temperature and concentrated in vacuo. This was then dissolved in a minimal amount of dichloromethane and purified on a Chromatotron (200 omicron plate) with 3% methanol/dichloromethane to give a residue which was recrystallized using ether/hexanes to give the title compound. 1H NMR: 8.45-8.55 (d, 1H, J=4 Hz), 8.35-8.40 (s, 1H), 7.75-7.80 (d, 1H, J=12 Hz), 7.65-7.70 (d, 1H, J=12 Hz), 7.20-7.35 (m, 5H), 7.15-7.20 (m, 1H), 7.00-7.05 (s, 1H), 4.85-4.95 (s, 2H), 3.05-3.15 (q, 2H, J=10z), 2.15-2.20 (s, 3H), 1.40-1.50 (t, 3H, J=8 Hz); MS calcd. 391.5; MS (M+1)=392.1.

Workup

  1. temperatureThis was refluxed for three hours
  2. temperaturerefluxed for two hours
  3. temperatureThe reaction was then cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThis was then dissolved in a minimal amount of dichloromethane
  6. custompurified on a Chromatotron (200 omicron plate) with 3% methanol/dichloromethane
  7. customto give a residue which
  8. customwas recrystallized

Sources & evidence

ORD record
ord-7d70624d0c3143a78fcc312e02c32c93
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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