Cesium carbonate → [3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine

HRID 1784815Notes

Reaction equation

HRID 1784815 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.B(O)(O)[C:26]1[CH:31]=[CH:30][C:29]2[O:32][CH2:33][O:34][C:28]=2[CH:27]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[O:32]1[C:29]2[CH:30]=[CH:31][C:26]([C:2]3[CH:3]=[C:4]([NH:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH:5]=[C:6]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=4)[CH:7]=3)=[CH:27][C:28]=2[O:34][CH2:33]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 50994028[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine

Product 1

HCID 68843561[3-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (MW=385.26, 193 mg, 0.5 mmol) was placed into a 10 mL microwave reaction tube and placed under a nitrogen atmosphere. 3,4-(Methylenedioxy)phenylboronic acid (MW=165.94, 124 mg, 0.75 mmol), 2-(di-t-butylphosphino)biphenyl (FW 298.41, 15 mg, 0.05 mmol), tris(dibenzylideneacetone)dipalladium (FW 915.75, 13 mg, 0.025 mmol), cesium carbonate (FW 325.82, 326 mg, 1 mmol) and dry dioxane (3 mL) were added to the tube. After flushing with nitrogen, the reaction tube was sealed and heated at 110° C. for 16 h. After cooling, the reaction mixture was filtered through a short pad of silica gel, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using 2% methanol in methylene chloride to give [3-benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine.

Workup

  1. customAfter flushing with nitrogen
  2. customthe reaction tube was sealed
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through a short pad of silica gel
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b47ffa855b54e379dbfcda0be4614a0
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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