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

HRID 857364

반응식

HRID 857364 반응식
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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 10421208Zinc bromide촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-adefbee9523c48e496956f009ebb9053
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144913B2

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