Dimethylformamide → Ethyl 8-(4-Methoxyphenyl)-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48914

반응식

HRID 48914 반응식
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[F-].[Cs+].CN(C=O)C>O.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]3=[O:17])=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 201262(4-Methoxyphenyl)boronic acidHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 20634155Ethyl 8-(4-Methoxyphenyl)-4-Oxo-4H-Quinolizine-3-Carboxylate수율 52.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

An oven-dried 50 ml round-bottom flask equipped with reflux condenser was purged with argon, followed by addition of ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate (2) (500 mg, 2 mmol), 4-methoxyphenylboronic acid (372 mg, 2.4 mmol), CsF (600 mg, 3.9 mmol), PdCl2[P(c-Hex)3]2 (80 mg, 0.1 mmol) and 6 ml DMF. The reaction mixture was stirred at 110° C. for 12 h and cooled to room temperature. Completion of the reaction was indicated by thin layer chromatography (ethyl acetate). The reaction mixture was poured into 100 ml water and extracted three times with 100 ml chloroform. The combined organic layers were washed three times with 50 ml water. The organic solvent was evaporated and the crude product was further purified by column chromatography (5% MeOH in ethyl acetate) to give a bright yellow solid (340 mg, 50% yield). M.p. 205-209° C. 1H NMR (δ, CDCl3): 1.43 (t, J=7 Hz, 3H), 3.90 (s, 3H), 4.42 (q, J=7 H, 2H), 6.65 (d, J=8 Hz, 1H), 7.05 (d, J=9 Hz, 2H), 7.43 (dd, J=2 Hz, J=7 Hz, 1H), 7.58-7.80 (m, 3H), 8.37 (d, J=8 Hz, 1H), 9.41 (d, J=7 Hz, 1H). MS: m/z 323.1159; required for C19H17NO4: 323.1157.

후처리

  1. customAn oven-dried 50 ml round-bottom flask equipped
  2. temperaturewith reflux condenser
  3. customwas purged with argon
  4. temperaturecooled to room temperature
  5. extractionextracted three times with 100 ml chloroform
  6. washThe combined organic layers were washed three times with 50 ml water
  7. customThe organic solvent was evaporated
  8. customthe crude product was further purified by column chromatography (5% MeOH in ethyl acetate)

출처 및 근거

ORD 기록
ord-e4fec1a4088f49eaaccdd469502b69ad
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706528B2

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