Dimethylformamide → HCID 67223545、化合物

HRID 1041841ノート

反応式

HRID 1041841 の反応式
CN(C)C=O.[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8](B(O)O)[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][C:29]([CH3:38])([CH3:37])[CH2:28][N:27]=1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:37][C:29]1([CH3:38])[CH2:28][N:27]=[C:26]([C:8]2[CH:7]=[N:6][C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30]1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2734663Quinoline-3-boronic acidHCID 67114181HCID 67114181、化合物

生成物 1

HCID 67223545HCID 67223545、化合物収率 53%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

After carrying out nitrogen replacement on a dimethylformamide solution (15 mL) of 3-quinoline boronic acid (0.70 g, 4.07 mmol) and 2 M aqueous cesium carbonate solution (4.70 mL, 9.40 mol), tetrakis(triphenylphosphine)palladium (0.72 g, 0.63 mmol) and 5-chloro-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine (3.13 mmol) were added to this solution. This solution was then stirred for 14 hours while heating at 90° C. Subsequently, the reaction solution was cooled to room temperature followed by pouring in ethyl acetate (50 mL) and water (50 ml) and filtering with celite. The filtrate was extracted with ethyl acetate (100 mL) and the organic layer was washed with brine (50 mL) followed by drying with magnesium sulfate. After filtering, the solvent was distilled off under reduced pressure to obtain 0.50 g (53%) of the target compound by purifying the resulting residue by silica gel column chromatography (hexane:ethyl acetate=2:1).

後処理

  1. additionwere added to this solution
  2. temperatureSubsequently, the reaction solution was cooled to room temperature
  3. filtrationwater (50 ml) and filtering with celite
  4. extractionThe filtrate was extracted with ethyl acetate (100 mL)
  5. washthe organic layer was washed with brine (50 mL)
  6. dry with materialby drying with magnesium sulfate
  7. filtrationAfter filtering
  8. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-08f9a7c8443645abb440304d220da3c0
出典データセット
uspto-grants-2013_10
特許番号
US08557738B2

反応ノート

読み込み中…