Potassium Carbonate → HCID 25014931, compound

HRID 501050Notes

Reaction equation

HRID 501050 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:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7351515-Bromopyridine-2-carboxamideHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 25014931HCID 25014931, compoundYield 0.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

2-Benzofuranboronic acid (3.1 mmol), 5-bromopyridine-2-carboxamide (3.7 mmol), 2M K2CO3 (aq., 6 mL) and Pd(dppf)Cl2 (0.31 mmol) were mixed and stirred at 80° C. in DMF for 2 h. The reaction mixture was filtered and washed with H2O and EtOAc. DMSO was added to the solid remains and filtered. The filtrate was collected and purified by reverse phase HPLC to afford the title compound as a white solid (2.5 mg). 1H NMR δ ppm 9.18 (d, 1 H) 8.46 (dd, 1 H) 8.13-8.19 (m, 2 H) 7.68-7.78 (m, 4 H) 7.43-7.30 (m, 2 H); MS m/z 239 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with H2O and EtOAc
  3. additionDMSO was added to the solid remains
  4. filtrationfiltered
  5. customThe filtrate was collected
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-0880102587af48ba80c021cb6eeea46b
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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