Triethylamine → Benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate

HRID 1600174Notes

Reaction equation

HRID 1600174 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[NH:6]2.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:34]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:37])[CH:35]=[CH2:36].C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.ClCCl>[CH3:11][C:5]1[NH:6][C:7]2[C:3]([CH:4]=1)=[C:2](/[CH:36]=[CH:35]/[C:34]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH:10]=[CH:9][CH:8]=2

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 75617Benzyl acrylateHCID 80271Tri-o-tolylphosphineHCID 218145664-Bromo-2-methyl-1H-indole

Product 1

HCID 86752481Benzyl (E)-3-(2-methyl-1H-indol-4-yl)-2-propenoate

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-bromo-2-methyl-1H-indole (containing 25% of the 6-bromo isomer) (8.30 g), palladium (II) acetate (0.45 g), tri-o-tolylphosphine (1.22 g), benzyl acrylate (9.76 g) and triethylamine (8.36 ml) in acetonitrile (8 ml) was heated in an oil bath at 140° C. under an atmosphere of nitrogen for 2 hours. The mixture was cooled and partitionedbetween dichloromethane and water. The organic layer was separated, washed three times with water and dried (MgSO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with dichloromethane/hexane (1:1) first gave impurity followed by pure product.The product fractions were evaporated and the residue was triturated with ether to give the title compound (6.60 g), m.p. 135°-136° C.Found: C,77.98; H,6.10; N,4.71. C19H17NO2 requires: C,78.33; H,5.88; N,4.81%. Further elution with dichloromethane/hexane (4:1) gave benzyl (E)-3-(2-methyl-1H-indol-6-yl)-2-propenoate (2.0 g), m.p. 164°-165° C. Found: C,78.53; H,6.06; N,4.74. C19 H17NO2 requires: C,78.33; H,5.88; N,4.81%.

Workup

  1. temperatureThe mixture was cooled
  2. customThe organic layer was separated
  3. washwashed three times with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customwas chromatographed on silica gel
  8. washElution with dichloromethane/hexane (1:1) first gave impurity
  9. customwere evaporated
  10. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-68f0609a41ec489db931c4998e6347f6
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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