Benzyl Alcohol → Benzyl 1-methyl-oxindole-5-carboxylate

HRID 1976780노트

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HRID 1976780 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6](=[O:12])[CH2:5]2.C(N(CC)CC)C.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C[O:31][CH2:30]C1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:30]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:31])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:12]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24326665-Bromo-1-methyl-2-oxoindoline

생성물 1

HCID 21998744Benzyl 1-methyl-oxindole-5-carboxylate

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

반응 조건

온도
130 °C

실험 절차

A solution of 5-bromo-1-methyl oxindole (3.75 g, 16.6 mmol) and triethylamine (3.48 mL) in THF (40 mL) was treated with benzyl alcohol (2.58 mL) and PdCl2(dppf) (300 mg), stirred under carbon monoxide (680 psi) at 130° C. for 16 hours, depressurized, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified on silica gel with 30% ethyl acetate/hexanes to provide 2.36 g of the desired product.

후처리

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated
  3. customThe concentrate was purified on silica gel with 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-e1162bedb14248e2ae3d2451e161fd4e
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228868B1

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