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

HRID 1600174ノート

反応式

HRID 1600174 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-68f0609a41ec489db931c4998e6347f6
出典データセット
uspto-grants-1998_04
特許番号
US05744488

反応ノート

読み込み中…