Cesium carbonate → HCID 11552467、化合物

HRID 747573ノート

反応式

HRID 747573 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>C(COC)OC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4]

参加物

7

反応物 3

HCID 10796Cesium carbonate2 回HCID 27339602-Thiopheneboronic acid2 回HCID 11537926HCID 11537926、化合物

生成物 1

HCID 11552467HCID 11552467、化合物収率 49.9%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a suspension of 0.462 g (0.0004 mol) tetrakis(triphenylphosphine)-palladium(0) in 45 ml dry dimethoxyethane, 5.00 g (0.0136 mol) (R)-5-[1-(4-bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester were added and stirred for 10 min at room temperature under nitrogen atmosphere. 3.65 g (0.0285 mol) thiophene-2-boronic acid in 20 ml ethanol and 14.3 ml (0.0286 mol) of a 2 M aqueous solution of Cs2CO3 were added and the mixture was heated to 75-80° C. for 3 hours. After 1.25 hours, another 0.5 equivalents of thiophene-2-boronic acid and Cs2CO3 were added to the mixture. The warm reaction mixture was filtered, the solid was washed with ethyl acetate and the solvent of the filtrates was evaporated. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and the solvent was removed. The crude product was recrystallized from n-butanol/n-heptane 1:2 and dried in vacuum to give 2.52 g (0.00678 mol) (R)-5-[1-(4-thiophen-2-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester.

後処理

  1. additionwere added
  2. temperaturethe mixture was heated to 75-80° C. for 3 hours
  3. waitAfter 1.25 hours
  4. customThe warm reaction mixture
  5. filtrationwas filtered
  6. washthe solid was washed with ethyl acetate
  7. customthe solvent of the filtrates was evaporated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customthe solvent was removed
  12. customThe crude product was recrystallized from n-butanol/n-heptane 1:2
  13. customdried in vacuum

出典と根拠

ORDレコード
ord-ad4c29073193481e9e071e38bfda27dc
出典データセット
uspto-grants-2008_07
特許番号
US07396944B2

反応ノート

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