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

HRID 1418423

반응식

HRID 1418423 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

A mixture of 2-trifluoromethanesulfonyloxy-5-pyridinecarboxylic 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(triphenylphosphine) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-037370866b484ec0b11ce18670854d1c
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883105

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