Iodine → HCID 91379151, 화합물

HRID 857369노트

반응식

HRID 857369 반응식
II.Br[CH:4]=[CH:5][CH3:6].[CH3:7][O:8][C:9](=[O:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18](Br)=[CH:19][C:20]([O:23][CH3:24])=[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:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18]([C:5]([CH3:6])=[CH2:4])=[CH:19][C:20]([O:23][CH3:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1

참가 물질

8

반응물 3

HCID 807IodineHCID 115331-Bromo-1-propeneHCID 58760742HCID 58760742, 화합물

생성물 1

HCID 91379151HCID 91379151, 화합물

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 10421208Zinc bromide촉매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
60 °C

실험 절차

To Mg (143 mg, 5.8 mmol) in THF (4 mL) with trace of I2 was added α-bromopropene (583 μL) in order to maintain a 60° C. exotherm. After 30 minutes, a solution of ZnBr2 (1.31 g, 5.8 mmol) in THF (4 mL) was added. The reaction mixture was heated at 55° C. for 1 hour, cooled to r.t. and (Pd (dppf) CH2Cl2 (50 mg) was added followed by CuI (18.5 mg). After 5 minutes a solution of methyl (8-bromo-6-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (Example 22, Step 5, 200 mg, 0.59 mmol) in THF (7 mL) was added and the mixture was refluxed for 1 hour, cooled, 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 (50 mg).

후처리

  1. temperatureThe reaction mixture was heated at 55° C. for 1 hour
  2. temperaturecooled to r.t.
  3. temperaturethe mixture was refluxed for 1 hour
  4. temperaturecooled
  5. customquenched 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-0854fb48adbd470db0cf99307948342c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144913B2

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