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

HRID 1418423

反応式

HRID 1418423 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-037370866b484ec0b11ce18670854d1c
出典データセット
uspto-grants-1999_03
特許番号
US05883105

関連ノート

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