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

HRID 1600174노트

반응식

HRID 1600174 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-68f0609a41ec489db931c4998e6347f6
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744488

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