Potassium Phosphate, Tribasic → HCID 67272898、化合物

HRID 1698543ノート

反応式

HRID 1698543 の反応式
Br[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)[CH3:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:14]

参加物

9

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 596354707-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

生成物 1

HCID 67272898HCID 67272898、化合物収率 64.4%

試薬・触媒・溶媒 5

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 280 mg (1.23 mmol) of 7-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one, 222 mg (1.48 mmol) of 2-ethylphenylboronic acid, 113 mg (0.0123 mmol) of tris(dibenzylideneacetone)dipalladium, 29 mg (0.0615 mmol) of X-Phos and 522 mg (2.46 mmol) of potassium phosphate in 9 mL of toluene was stirred at 100° C. for 4 hours. After cooling, the reaction mixture was diluted with water and ethyl acetate and passed through celite. The filtrate was extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-65% ethylacetate/n-hexane gradient mixture to give 200 mg (64%) of the title compound.

後処理

  1. temperatureAfter cooling
  2. extractionThe filtrate was extracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 25-65% ethylacetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-8329c926b35c499d86bb5246c45e9d14
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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