Toluene → methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate

HRID 915586

反応式

HRID 915586 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[N:16]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:29](B(O)O)[CH3:30].C(Cl)Cl.C1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:25]([C:15]1[CH:14]=[C:13]([NH:12][C:5]2[CH:4]=[CH:3][C:2]([CH2:29][CH3:30])=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[N:16]=1)([CH3:28])([CH3:27])[CH3:26]

参加物

7

反応物 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 521157Ethylboronic acidHCID 58958623methyl 5-bromo-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoate

生成物 1

HCID 58958598methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-5-ethylbenzoate収率 61%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

To a mixture of methyl 5-bromo-2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoate (Example 234, 1.15 g, 4.13 mmol), ethylboronic acid (1.16 g, 15.7 mmol), and Pd(dppf)Cl2.CH2Cl2 (114 mg, 0.16 mmol) was added toluene (20 mL) and dioxane (5 mL). The resulting solution was degassed under nitrogen for 30 min, followed by addition of sodium bicarbonate (2 M aq solution, 15 mL). The mixture was then heated to 85° C. for 16 h. The reaction mixture was allowed to cool to rt. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash chromatography using 0 to 10% ethyl acetate in hexanes to afford 606 mg (61%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 9.17 (s, 1H), 7.68 (s, 1H), 7.22-7.33 (m, 6H), 6.08 (s, 1H), 3.70 (s, 3H), 2.51 (q, 2H), 2.05 (s, 3H), 1.30 (s, 9H), 1.14 (t, 3H). ES-MS m/z 392.2 (MH+); HPLC RT (min) 4.62.

後処理

  1. customThe resulting solution was degassed under nitrogen for 30 min
  2. additionfollowed by addition of sodium bicarbonate (2 M aq solution, 15 mL)
  3. temperatureto cool to rt
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-c32987e78db14c6d91d9166ea5590b2e
出典データセット
uspto-grants-2007_09
特許番号
US07265144B2

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