Sodium Carbonate → Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate

HRID 511541

반응식

HRID 511541 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([CH3:12])[C:7]2=[O:13].CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[CH3:12][C:8]1[C:7](=[O:13])[C:6]2[C:11](=[C:2]([C:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH:26]=3)[CH:3]=[CH:4][C:5]=2[N+:14]([O-:16])=[O:15])[NH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 592787964-(4,4,5,5-Tetramethyl-(1,3,2)dioxaborolan-2-yl)cyclohex-3-ene-1-carboxylic acid ethyl esterHCID 672543158-bromo-3-methyl-5-nitroquinolin-4(1H)-one2회

생성물 1

HCID 67254537Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate수율 67%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

A mixture of 8-bromo-3-methyl-5-nitroquinolin-4(1H)-one (Compound 304E, 700 mg, 2.47 mmol), ethyl 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)cyclohex-3-enecarboxylate (1.8 g, 6.43 mmol, commercially available or can be prepared according to WO2008/099221), Pd(PPh3)4 (20 mg), and Na2CO3 (1 g, 9.43 mmol) in 1,4-dioxane/H2O (150 mL, 4:1) was evacuated and purged with N2. The reaction mixture was stirred at 100° C. for 18 h under N2. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The material was purified by flash column chromatography to afford the desired compound (600 mg, yield: 67%). 1H NMR (DMSO-d6, 400 MHz): δ=1.22 (t, J=7.2 Hz, 3 H), 1.85 (m, 1 H), 1.96 (s, 3 H), 2.08 (m, 1 H), 2.26 (m, 1 H), 2.38-2.49 (m, 3 H), 2.78 (m, 1 H), 4.12 (q, J=7.2 Hz, 2 H), 5.84 (s, 1 H), 7.46 (d, J=8.0 Hz, 1 H), 7.58 (d, J=8.0 Hz, 1 H), 7.83 (d, J=6.0 Hz, 1 H), 10.94 (d, J=6.0 Hz, 1 H).

후처리

  1. customcommercially available or can be prepared
  2. customwas evacuated
  3. custompurged with N2
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-048c8d3ef5364b72a5bd2b24ef271d78
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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