Potassium Carbonate → HCID 58356356, compound

HRID 244737Notes

Reaction equation

HRID 244737 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.Br[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[C:16]([NH:23][C:24]([C:26]2[N:27]=[C:28]([CH3:31])[S:29][CH:30]=2)=[O:25])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[C:16]([NH:23][C:24]([C:26]2[N:27]=[C:28]([CH3:31])[S:29][CH:30]=2)=[O:25])[CH:15]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 58255750N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide

Product 1

HCID 58356356HCID 58356356, compoundYield 3.2%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of 1-benzofuran-2-ylboronic acid (24 mg, available from Lancaster Synthesis) in 1,4-dioxane (1 ml) was added a solution of .N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (34 mg) in 1,4-dioxane (1 ml). A solution of potassium carbonate (17 mg) in water (0.2 ml) was then added, followed by Pd(dppf)Cl2 (10 mg). The reaction vessel was sealed and heated under microwave irradiation in CEM Discover at 150° C. for 30 min. The mixture was cooled and the solvent was evaporated in vacuo using the Genevac to give the crude products. The sample was loaded in methanol and applied to a reverse phase (C18) cartridge (500 mg) and eluted using MeCN/TFA 0.1% (3×3 ml). The appropriate fractions were combined and dried under a stream of nitrogen then the residue was dissolved in (3:1, DMSO:MeOH, 0.5 ml) and purified by mass directed preparative HPLC (Method C) to afford the title compound (1.2 mg).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated in vacuo
  4. customto give the crude products
  5. washeluted
  6. customdried under a stream of nitrogen
  7. dissolutionthe residue was dissolved in (3:1, DMSO:MeOH, 0.5 ml)
  8. custompurified by mass

Sources & evidence

ORD record
ord-3383dc7981b1428b8eec115482a5bb6c
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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