Cesium carbonate → Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243023ノート

反応式

HRID 2243023 の反応式
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][N:8]=1)=[O:5])[CH3:2].I[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]2=[O:42].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[N:8]=[CH:9][C:10]([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[C:27]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]3=[O:42])=[CH:11][CH:12]=1)[CH3:2]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 592084346-(3-Ethylureido)pyridine-3-boronic acid pinacol ester2 回HCID 59208478Ethyl 6-iodo-1-[2-(methyloxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate

生成物 1

HCID 59208515Ethyl 6-(6-(3-ethylureido)pyridin-3-yl)-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

試薬・触媒・溶媒 3

HCID 57646695Palladium;tetraphenyl-lambda5-phosphane触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of N-ethyl-N′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)urea (Intermediate 1, 80 mg, 0.27 mmol), ethyl 6-iodo-1-(2-methoxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (WO2006010733, 100 mg, 0.25 mmol), cesium carbonate (90 mg, 0.27 mmol), and Tetrakisphenylphosphine palladium (28.9 mg, 0.02 mmol) in dioxane (4 mL) and water (1 mL) was degassed with nitrogen for 30 minutes. The reaction mixture was then heated in a microwave for 1 h at 110° C. The reaction mixture was cooled to room temperature and filtered, then placed on high vacuum to remove residual solvent (59 mg). MS (ESP): 439 (M+H+) for C23H26N4O5; NMR: 9.34 (s, 1H), 8.61 (m, 2H), 8.45 (m, 1H), 8.10 (m, 1H), 8.09 (m, 2H), 7.54 (m, 1H), 4.62 (m, 2H), 4.25 (m, 2H), 3.71 (m, 2H), 3.57 (s, 3H), 3.21 (m, 2H), 1.30 (t, J=7 Hz, 3H), 1.11 (t, J=8 Hz, 3H).

後処理

  1. customwas degassed with nitrogen for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove residual solvent (59 mg)

出典と根拠

ORDレコード
ord-0b121e4ab7dd415d82270f905ac0474e
出典データセット
uspto-grants-2010_03
特許番号
US07674801B2

反応ノート

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