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

HRID 1976780ノート

反応式

HRID 1976780 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
130 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e1162bedb14248e2ae3d2451e161fd4e
出典データセット
uspto-grants-2001_05
特許番号
US06228868B1

反応ノート

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