Dichloromethane → 3-(4-Fluorophenyl)-5-nitro-1H-indazole

HRID 227699ノート

反応式

HRID 227699 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[NH:4][N:3]=2)=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 222608361-Boc-3-bromo-5-nitro-1H-indazole

生成物 1

HCID 534397423-(4-Fluorophenyl)-5-nitro-1H-indazole収率 100%

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
95 °C

実験手順

The product from Step (b) (0.5 g, 1.5 mmol), 4-fluoro phenylboronic acid (0.31 g, 2.2 mmol) and Pd(dppf)2Cl2.CH2Cl2 (0.12 g, 0.15 mmol) were combined in 9 ml of 2:1 Dioxane/2 M K2CO3 The reaction mixture was sealed and heated to 95° C. for 18 h. The resulting biphasic mixture was cooled to room temperature. The phases were separated and the organic phase (top) was filtered. The aqueous layer was extracted once with EtOAc. The combined organic phases were washed with sat'd NaHCO3, water, brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5% MeOH/CH2Cl2) to afford 0.37 g of the title compound, (100%); MS (ES+) m/e 259 [M+H]+.

後処理

  1. customwas sealed
  2. temperatureThe resulting biphasic mixture was cooled to room temperature
  3. customThe phases were separated
  4. filtrationthe organic phase (top) was filtered
  5. extractionThe aqueous layer was extracted once with EtOAc
  6. washThe combined organic phases were washed with sat'd NaHCO3, water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-26ae3449e1e54625a1aa31e2d7e2bb03
出典データセット
uspto-grants-2009_07
特許番号
US07560467B2

反応ノート

読み込み中…