Iodine → HCID 91379151, compound

HRID 857369Notes

Reaction equation

HRID 857369 reaction equation
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

Participants

8

Reactant 3

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

Product 1

HCID 91379151HCID 91379151, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0854fb48adbd470db0cf99307948342c
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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