Benzo(B)Thiophene-2-Boronic Acid → HCID 46228238, compound

HRID 1965914Notes

Reaction equation

HRID 1965914 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[S:12]1[C:16](B(O)O)=[CH:15][C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:2]=[N:3][C:4]=1[C:16]1[S:12][C:13]2[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=2[CH:15]=1

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 46228238HCID 46228238, compoundYield 78.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Compound 2 (5.0 g, 29.1 mmol), benzo[b]thiophene-2-ylboronic acid (6.23 g, 35.0 mmol), and tetrakis-(triphenylphosphine) palladium(0) (1.07 g, 0.87 mmol) were added to an RBF equipped with a reflux condenser and dissolved in a mixed solvent system of toluene (150 mL) and ethanol (50 mL). After addition of 50 mL of aqueous 2 N sodium carbonate solution, the reaction mixture was heated at 80° C. for 2 days. The organic phase was separated and extracted with methylene chloride. The organics were then combined, dried over Na2SO4 and filtered. The solvent was evaporated to give the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:30 v/v) to yield 6.12 g (78%) of methyl 6-(benzo[b]thiophen-2-yl)nicotinate (Compound 3).

Workup

  1. customequipped with a reflux condenser
  2. customThe organic phase was separated
  3. extractionextracted with methylene chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customto give the crude product
  8. customThe resulting crude product was then purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:30 v/v)

Sources & evidence

ORD record
ord-afd7a4eaa4334500906d5ff8a0bdecf0
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

Loading…