Potassium Phosphate, Tribasic → Methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate

HRID 1865215노트

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HRID 1865215 반응식
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][O:8][C:4]=2[CH:3]=1.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][CH:17]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:28][CH3:29])[N:19]=[CH:18][CH:17]=[C:16]2[O:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][O:8][C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, Tribasic2회HCID 4596104-Chloro-6,7-dimethoxyquinoline3회HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3회HCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

생성물 1

HCID 69019235Methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매3회HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Methyl 6-hydroxybenzofuran-3-carboxylate (312 mg, 1.62 mmol) was dissolved in N,N-dimethylformamide (5 mL) then added 4-chloro-6,7-dimethoxyquinoline (451 mg, 2.02 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (77 mg, 0.162 mmol), palladium acetate (36 mg, 0.162 mmol) and potassium phosphate (687 mg, 3.24 mmol). The reaction mixture was stirred at 100° C. overnight. Additional palladium acetate (36 mg, 0.162 mmol) was added to the mixture and the heating was continued at 100° C. for 4 h. Additional 4-chloro-6,7-dimethoxyquinoline (181 mg, 0.812 mmol) and 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (77 mg, 0.162 mmol) were added to the mixture and heating at 100° C. was continued for 2 days. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The remaining orange oil was redissolved in toluene (5 mL) and DMF (1 mL) then added 4-chloro-6,7-dimethoxyquinoline (225 mg, 1.01 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (38 mg, 0.080 mmol), palladium acetate (18 mg, 0.080 mmol) and potassium phosphate (343 mg, 1.62 mmol). The reaction mixture was heated at 100° C. overnight and concentrated in vacuo. The remaining orange-black oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane) to afford methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate as a light yellow solid. MS (ESI, pos. ion) m/z: 380.1 (M+1).

후처리

  1. waitthe heating was continued at 100° C. for 4 h
  2. temperatureheating at 100° C.
  3. waitwas continued for 2 days
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe remaining orange oil was redissolved in toluene (5 mL)
  7. temperatureThe reaction mixture was heated at 100° C. overnight
  8. concentrationconcentrated in vacuo
  9. customThe remaining orange-black oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-e6311db453e7497696d477d60e619465
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626030B2

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