1,2-Dimethoxyethane → 6-(Thiophen-2-Yl)Pyridine-3-Carboxylic Acid

HRID 1004607Notes

Reaction equation

HRID 1004607 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][N:8]=1)(=O)=O.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O.[OH-].[Ba+2].[OH-].COCCOC>[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.O>[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 27339602-Thiopheneboronic acidHCID 6093286Barium hydroxideHCID 154111432-Trifluoromethanesulfonyloxy-5-pyridinecarboxylic acid

Product 1

HCID 154111446-(Thiophen-2-Yl)Pyridine-3-Carboxylic Acid

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-trifluoromethanesulfonyloxy-5-pyridine-carboxylic acid (0.442 g, 1.72 mmol), 2-thienylboronic acid (1.56 g, 12.79 mmol), barium hydroxide (0.813 mg, 2.58 mmol), DME (8 mL) and water (1.5 mL) is purged with dry argon. Tetrakis(triphenyl-phosphine) palladium(0) (99.0 mg, 0.086 mmol) is added, and the resultant solution is stirred at 80° C. for 4 hours. The solvents are evaporated in vacuo, and the residue is partitioned between EtOAc and water. The aqueous extract is separated, and extracted with EtOAc. The organic extracts are combined, washed with sat. aq. NaHCO3 and 5% aq. Na2S2O3, dried, (Na2SO4) and the solvent is evaporated in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. customis purged with dry argon
  2. customThe solvents are evaporated in vacuo
  3. customthe residue is partitioned between EtOAc and water
  4. extractionThe aqueous extract
  5. customis separated
  6. extractionextracted with EtOAc
  7. washwashed with sat. aq. NaHCO3 and 5% aq. Na2S2O3
  8. customdried
  9. custom(Na2SO4) and the solvent is evaporated in vacuo
  10. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-decd5796fac84f568afe440fd831a831
Source dataset
uspto-grants-2000_04
Patent number
US06051574

Reaction notes

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