6-Bromo-4-methoxy-1H-indole → 1H-Indole, 6-ethenyl-4-methoxy-

HRID 2421232Notes

Reaction equation

HRID 2421232 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13](C([Sn])=C(CCCC)CCCC)[CH2:14]CC>COCCOC.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:13]([C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([O:11][CH3:12])[CH:3]=1)=[CH2:14]

Participants

5

Reactant 2

HCID 247280346-Bromo-4-methoxy-1H-indoleHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 596279181H-Indole, 6-ethenyl-4-methoxy-Yield 113.3%

Reagents, catalysts & solvents 2

HCID 178424406HCID 178424406, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6-bromo-4-(methyloxy)-1H-indole (900 mg, 3.98 mmol) in 1,2-dimethoxyethane (20 mL) was added tributylvinyltin (1.74 mL, 5.96 mmol). The reaction mixture was degassed with argon and then treated with dichlorobis(tri-o-tolylphosphine)palladium (153 mg, 0.19 mmol). The mixture was heated at 90° C. for 65 hours. The mixture was filtered through a pad of celite, washed with ethyl acetate and then the filtrate concentrated in vacuo. The product was purified by silica gel chromatography eluting with 2-50% ethyl acetate in hexane to yield the title compound (D8), (781 mg).

Workup

  1. customThe reaction mixture was degassed with argon
  2. filtrationThe mixture was filtered through a pad of celite
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe product was purified by silica gel chromatography
  6. washeluting with 2-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6a76e5a2ebf94c57aea9cde4bf2cfcf2
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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