Potassium Carbonate → HCID 58480078, compound

HRID 391500Notes

Reaction equation

HRID 391500 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=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[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:3]=[C:2]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58479943HCID 58479943, compound

Product 1

HCID 58480078HCID 58480078, compound

Reagents, catalysts & solvents 2

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

Procedure

4.74 g (12.8 mmol) of 2-(3,5-dibromophenyl)benzo[d]thiazole) according to Synthesis Example 5, 1.89 g (15.4 mmol) of pyridine-3-boronic acid, 0.44 g (3 mol %) of tetrakis(triphenylphosphine)palladium (0), and 5.31 g (38.4 mmol) of potassium carbonate were dissolved in 50 ml of tetrahydrofuran/H2O mixed in a volume ratio of 4/1. 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. The extract was separated through a column and dried, obtaining 2.54 g (Y=54%) of a white solid.

Workup

  1. additionmixed in a volume ratio of 4/1
  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 extract was separated through a column
  7. customdried
  8. customobtaining 2.54 g (Y=54%) of a white solid

Sources & evidence

ORD record
ord-1bc965888ce94d1092d0ca6ff1e6a794
Source dataset
uspto-grants-2013_02
Patent number
US08383932B2

Reaction notes

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