Sodium Carbonate → 1,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one

HRID 270685ノート

反応式

HRID 270685 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:29])[N:7]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Cl[C:54]1[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1(P([Pd-3](Cl)(Cl)(P(C2C=CC=CC=2)C2C=CC=CC=2)[C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[F:28][C:25]([F:27])([F:26])[C:22]1[CH:23]=[CH:24][C:19]([N:7]2[C:6](=[O:29])[C:5]3[C:9](=[CH:10][C:2]([C:54]4[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=4)=[CH:3][CH:4]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])=[CH:20][CH:21]=1

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2733548Bis(pinacolato)diboraneHCID 692032346-Bromo-1,2-dihydro-2-(4-trifluoromethylphenyl)-1-(2-trimethylsilyl ethoxymethyl)-3H-indazol-3-one

生成物 1

HCID 866128481,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one収率 13.9%

試薬・触媒・溶媒 2

HCID 178479788HCID 178479788、化合物触媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

The product of Step 5 (1.3 g, 2.6 mmol), was dissolved in dioxane (10 mL) and flushed with N2. Bis(pinacolato)diboron (680 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (60 mg) and KOAc (380 mg, 3.9 mmol) were added. The mixture was stirred at 100° C. overnight. 2-Chloro-3-trifluoromethylpyridine (470 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (20 mg) and saturated Na2CO3 solution (1 mL) were added, and the mixture heated at reflux for a further 18 h. Purification by column chromatography gave 0.2 g of product as an oil.

後処理

  1. customflushed with N2
  2. temperaturethe mixture heated
  3. temperatureat reflux for a further 18 h
  4. customPurification by column chromatography

出典と根拠

ORDレコード
ord-966c5ef759ed41eaadad4c4e9772a7c0
出典データセット
uspto-grants-2008_11
特許番号
US07449585B2

反応ノート

読み込み中…