Benzo(B)Thiophene-2-Boronic Acid → 5-(1-Benzothien-2-yl)pyridine-2-carboxamide

HRID 501049

Reaction equation

HRID 501049 reaction equation
[S: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]>[S: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 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 7351515-Bromopyridine-2-carboxamide

Product 1

HCID 250149305-(1-Benzothien-2-yl)pyridine-2-carboxamideYield 3.6%

Reagents, catalysts & solvents 2

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

Procedure

2-Benzothienylboronic acid (1.8 mmol), 5-bromopyridine-2-carboxamide (1.2 mmol), 2M K2CO3 (2.4 mL), Pd(dppf)Cl2 (0.12 mmol) were mixed and stirred at 80° C. in DMF for 3 h. The reaction mixture was filtered and to the filtrated was added EtOAc and H2O. The layers were separated and the aqueous phase was extracted twice with EtOAc. The organic extracts were dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid. The crude was subjected to reverse phase HPLC to afford the title compound as a light brown solid (11 mg). 1H NMR δ ppm 9.07 (d, 1 H) 8.34 (dd, 1 H) 8.24-8.02 (m, 5 H) 7.73 (s br, 1 H) 7.54-7.37 (m, 2 H); MS m/z 255 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered and to the filtrated
  2. additionwas added EtOAc and H2O
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. customThe solvent was evaporated in vacuo
  7. customto give a brown solid

Sources & evidence

ORD record
ord-a032e3afb19e418595dd11b2e977e424
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Linked notes

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