Toluene → 5-(Pyridin-3-yl)thiophene-2-carbaldehyde

HRID 1421536ノート

反応式

HRID 1421536 の反応式
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=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.CO>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:10]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11435467(5-Bromothiophen-2-yl)methanol

生成物 1

HCID 108994275-(Pyridin-3-yl)thiophene-2-carbaldehyde収率 98%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 153 mg (5-bromo-thiophen-2-yl)-methanol, 128 mg pyridine-3-boronic acid, and 64 mg tetrakis(triphenylphosphine) palladium was added solvent (7.3 mL toluene and 3.1 mL methanol) followed by 1.4 mL of 2.5M sodium carbonate and the mixture heated to 80° C. on an oil bath. After 16 hours the mixture was cooled to room temperature and cocncentrated in vacuo. The residue was solvated in ethyl acetate was washed sequentially with 0.5N sodium hydroxide and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 60:40; then 55:45) gave the title compound (147 mg).

後処理

  1. temperatureAfter 16 hours the mixture was cooled to room temperature
  2. washwas washed sequentially with 0.5N sodium hydroxide and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (hexane

出典と根拠

ORDレコード
ord-6d1d548fb35c4ea4a84adebc3912f6e5
出典データセット
uspto-grants-2000_06
特許番号
US06077858

反応ノート

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