Methyl Acrylate → 2-anilino-6-[(E)-3-methoxy-3-oxo-1-propenyl]-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one

HRID 2183810노트

반응식

HRID 2183810 반응식
[NH:1]([C:8]1[N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][C:13](Br)=[C:12]([CH3:20])[N:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:46]([O:50][CH3:51])(=[O:49])[CH:47]=[CH2:48]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH:1]([C:8]1[N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[N:11]=[C:12]([CH3:20])[C:13](/[CH:48]=[CH:47]/[C:46]([O:50][CH3:51])=[O:49])=[CH:14][C:15]=2[C:16](=[O:18])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 7294Methyl AcrylateHCID 11776TriphenylphosphineHCID 219482082-anilino-6-bromo-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one

생성물 1

HCID 115388182-anilino-6-[(E)-3-methoxy-3-oxo-1-propenyl]-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one수율 24.3%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To a suspension of 2-anilino-6-bromo-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (41 mg, 0.1 mmol) in DMF (2.0 mL) were successively added Pd(OAc)2 (0.70 mg, 0.003 mmol), Ph3P (5.2 mg, 0.02 mmol), TEA (0.03 mL) and methyl acrylate (17.2 mg, 0.2 mmol). The suspension was heated at 120° C. in a sealed tube for 64 h. The residue obtained after concentration in vacuo was washed with water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification by prep-HPLC provided methyl (2E)-3-(7-anilino-2-methyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridin-3-yl)-2-propenoate (10.0 mg, 24%): LCMS RT: 2.61 min, MH+: 412.3, Rf=0.26 (1:1 EtOAc:Hex).

후처리

  1. customThe residue obtained
  2. concentrationafter concentration in vacuo
  3. washwas washed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification

출처 및 근거

ORD 기록
ord-6bfd13c452c34f53b757ac314a819992
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900205B2

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