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

HRID 1421536노트

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HRID 1421536 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6d1d548fb35c4ea4a84adebc3912f6e5
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077858

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