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

HRID 511541

反応式

HRID 511541 の反応式
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

参加物

6

反応物 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)-one2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-048c8d3ef5364b72a5bd2b24ef271d78
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

関連ノート

読み込み中…