Potassium Phosphate, Tribasic → 5-(4-Cyclohexylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646132ノート

反応式

HRID 646132 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:56]1([C:62]2[CH:67]=[CH:66][C:65](B(O)O)=[CH:64][CH:63]=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1.C([O-])(O)=O.[Na+]>CCO.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:59]1[CH:58]=[CH:57][C:56]([CH:62]3[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]3)=[CH:61][CH:60]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

9

反応物 5

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 516892Sodium BicarbonateHCID 45891894-Cyclohexylbenzeneboronic acidHCID 687002455-Bromo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

生成物 1

HCID 686997835-(4-Cyclohexylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester収率 93%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

A mixture of 5-bromo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (154 mg, 0.38 mmol), K3PO4 (282 mg, 1.83 mmol), Pd(OAc)2 (4.5 mg, 0.02 mmol), tri(o-tolyl)phosphine (12 mg, 0.04 mmol), and toluene (3.5 mL) was stirred under argon for 25 min at room temperature. 4-Cyclohexylphenylboronic acid (117 mg, 0.57 mmol) in EtOH (0.5 mL) was added and the mixture was heated at reflux for 1 h. The mixture was allowed to cool, poured into NaHCO3 (aq. sat.), and extracted wait EtOAc. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by chromatography to give the sub-title compound (170 mg, 93%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureto cool
  4. extractionextracted
  5. waitwait EtOAc
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by chromatography

出典と根拠

ORDレコード
ord-5c8d24a2873540c4a443981c151a4e78
出典データセット
uspto-grants-2010_04
特許番号
US07705023B2

反応ノート

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