Potassium Carbonate → HCID 58480007, compound

HRID 391498Notes

Reaction equation

HRID 391498 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12]3[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=3[N:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.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>[Br:8][C:6]1[CH:5]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:12]3[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=3[N:10]=2)[CH:3]=[C:2]([C:26]2[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 59439661HCID 59439661, compound

Product 1

HCID 58480007HCID 58480007, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

9.4 g (22.0 mmol) of 2-(3,5-dibromophenyl)-1-phenyl-1H-benzo[d]imidazole according to Synthesis Example 3, 2.7 g (22.0 mmol) of pyridine-3-boronic acid, 0.76 g (3 mol %) of tetrakis(triphenylphosphine)palladium (0), and 6.1 g (44.0 mmol) of potassium carbonate were dissolved in 300 ml of tetrahydrofuran/H2O mixed in a volume ratio of 2/1. The solution was reacted at 80° C. for 12 hours. The acquired reactant was extracted with ethyl acetate and treated under reduced pressure to remove the solvent therein. The reactant was separated through a column and dried, obtaining 5.15 g (Y=54%) of a yellow solid.

Workup

  1. additionmixed in a volume ratio of 2/1
  2. customThe solution was reacted at 80° C. for 12 hours
  3. extractionThe acquired reactant was extracted with ethyl acetate
  4. additiontreated under reduced pressure
  5. customto remove the solvent
  6. customThe reactant was separated through a column
  7. customdried
  8. customobtaining 5.15 g (Y=54%) of a yellow solid

Sources & evidence

ORD record
ord-f25b2799390640d1860e2f8d6cef275f
Source dataset
uspto-grants-2013_02
Patent number
US08383932B2

Reaction notes

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