Iodine → Methyl[8-isopropenyl-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

HRID 857364

反応式

HRID 857364 の反応式
Br[CH:2]=[CH:3][CH3:4].II.[CH3:7][O:8][C:9](=[O:28])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18](Br)=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1>C1COCC1.[Zn+2].[Br-].[Br-].[Pd].[Cu]I>[CH3:7][O:8][C:9](=[O:28])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18]([C:3]([CH3:4])=[CH2:2])=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1

参加物

8

反応物 3

HCID 807IodineHCID 115331-Bromo-1-propeneHCID 131726144Methyl[8-bromo-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

生成物 1

HCID 90964995Methyl[8-isopropenyl-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate収率 72%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 10421208Zinc bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
55 °C

実験手順

Alpha-bromopropene (514 μL, 5.2 mmol) was added portionwise, in order to maintain 55° C. exotherm, to Mg (126 mg, 5.2 mmol) (in THF 4 mL) and a trace of iodine. The mixture was heated and stirred for 30 minutes. Dried ZnBr2 (1.16 g, 5.2 mmol) in THF (4 mL) was added and the mixture was heated at 55° C. for 1 hour. The reaction mixture was cooled to room temperature, and Pd (dppf) CH2Cl2 (19 mg) was added followed by CuI (7 mg) after a further 5 minutes. The product of Step 1 (200 mg, 0.52 mmol) in 3 ml THF was then added. The reaction mixture was heated to 75° C. for 15 minutes. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (130 mg).

後処理

  1. temperatureThe mixture was heated
  2. temperaturethe mixture was heated at 55° C. for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. temperatureThe reaction mixture was heated to 75° C. for 15 minutes
  5. customThe reaction was quenched with saturated aqueous NH4Cl
  6. extractionextracted with EtOAc
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-adefbee9523c48e496956f009ebb9053
出典データセット
uspto-grants-2006_12
特許番号
US07144913B2

関連ノート

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