Water → 2,5-Dichloro-pyridine-3-carbaldehyde

HRID 11680

반응식

HRID 11680 반응식
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([SnH](CCCC)CCCC)CCC.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:7][C:8]([Cl:11])=[CH:9][N:10]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 5948TributylstannaneHCID 27999962,5-Dichloro-nicotinoyl chloride

생성물 1

HCID 219732742,5-Dichloro-pyridine-3-carbaldehyde수율 34.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,5-Dichloro-nicotinoyl chloride (15 g, 0.071 mol) in tetrahydrofuran was added tributyl-stannane (24.9 g, 0.086 mol) portionwise over 45 minutes. The resulting mixture was stirred at ambient temperature for 50 minutes, and then treated with tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.00071 mol). The reaction mixture was stirred at ambient temperature for 4 hours, poured into water; the product was extracted with ethylacetate, the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate gave the title compound (4.3 g).

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  2. extractionthe product was extracted with ethylacetate
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customSilica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate

출처 및 근거

ORD 기록
ord-38c6d934eb854ee7a469257bfdad0650
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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