Tetrahydrofuran → Ethyl 3-(7-methoxyquinolin-4-yl)propanoate

HRID 40182

반응식

HRID 40182 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[Br-].[CH2:33]([O:35][C:36](=[O:40])[CH2:37][CH2:38][Zn+])[CH3:34].C1COCC1>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].[OH-].[NH4+]>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH2:38][CH2:37][C:36]([O:35][CH2:33][CH3:34])=[O:40])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 106078294-Chloro-7-methoxyquinolineHCID 178471816HCID 178471816, 화합물

생성물 1

HCID 67503802Ethyl 3-(7-methoxyquinolin-4-yl)propanoate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 14923Ammonium Hydroxide용매

실험 절차

4-chloro-7-methoxyquinoline (0.35 g, 2 mmol), tri-t-butylphosphonium tetrafluoroborate (0.05 g, 0.2 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.08 g, 0.09 mmol) were combined. The reaction vessel was purged and flushed with nitrogen three times, followed by addition of 3-ethoxy-3-oxopropylzinc bromide in THF (10 mL, 5 mmol, 0.5 M). The reaction mixture was microwaved at 150° C. for 60 minutes. Upon completion, ammonium hydroxide (10 mL) was added. After 30 minutes the mixture was filtered and the filtrate was partitioned between water and ethyl acetate. Extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated. Purified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2. (ESI, pos. ion) m/z: 354.1 (M+H).

후처리

  1. customThe reaction vessel was purged
  2. customflushed with nitrogen three times
  3. customThe reaction mixture was microwaved at 150° C. for 60 minutes
  4. filtrationAfter 30 minutes the mixture was filtered
  5. customthe filtrate was partitioned between water and ethyl acetate
  6. extractionExtracted with ethyl acetate (3×20 mL)
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customPurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-2749dc371527437e9924f4eb2acea80b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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