Dimethylformamide → HCID 67223545, 화합물

HRID 1041841노트

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HRID 1041841 반응식
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

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2734663Quinoline-3-boronic acidHCID 67114181HCID 67114181, 화합물

생성물 1

HCID 67223545HCID 67223545, 화합물수율 53%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08f9a7c8443645abb440304d220da3c0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557738B2

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