Potassium Carbonate → 4-[2-(2,6-Difluorophenyl)-4,5-dihydro-4-oxazolyl]-(4-fluorophenyl)methanone

HRID 964316ノート

反応式

HRID 964316 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)[N:13]=1.[F:21]C1C=CC(B(O)O)=CC=1.[C:31](=[O:34])([O-])[O-].[K+].[K+].[C]=O>C1(OC)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2([F:21])[CH:19]=[CH:18][C:17]([CH:31]=[O:34])=[CH:16][CH2:15]2)[N:13]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 11058111Oxazole, 2-(2,6-difluorophenyl)-4,5-dihydro-4-(4-iodophenyl)-HCID 178418416HCID 178418416、化合物

生成物 1

HCID 1317207194-[2-(2,6-Difluorophenyl)-4,5-dihydro-4-oxazolyl]-(4-fluorophenyl)methanone収率 276.6%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 7519Anisole溶媒

反応条件

温度
80 °C

実験手順

The compound of Example 2 (0.5 g, 1.3 mmol) and 4-fluorophenyl boronic acid (0.27 g, 2 mmol) and potassium carbonate (fine mesh, 0.5 g, 0.4 mmol) were suspended in anisole (15 mL) and carbon monoxide was bubbled through the mixture for 5 min. Bis (triphenylphosphine) palladium chloride (0.03 g, 0.50 mmol) was added and the mixture was evacuated and carbon monoxide was released into the reaction by means of a balloon. The evacuation and carbon monoxide release was repeated and the reaction was heated to 80° C. under a carbon monoxide atmosphere for 3 h. The anisole was removed under reduced pressure and the residue was partitioned between diethylether (50 mL) and water (50 mL). The ether solution was dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to silica gel chromatography with hexanes/ethyl acetate (5:1) as eluent to give the title compound (0.34 g) as a solid: m.p.: 105°-106° C. 1H NMR (CDCl3, 400 MHz) δ 7.9-7.0 (m,1H), 5.6 (m,1H), 4.9 (m,1H), 4.3 (m,1H).

後処理

  1. customcarbon monoxide was bubbled through the mixture for 5 min
  2. customthe mixture was evacuated
  3. customcarbon monoxide was released into the reaction by means of a balloon
  4. customThe anisole was removed under reduced pressure
  5. customthe residue was partitioned between diethylether (50 mL) and water (50 mL)
  6. dry with materialThe ether solution was dried over magnesium sulfate
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-f16619bcf3ce43f49f45edebd89ac27f
出典データセット
uspto-grants-1998_06
特許番号
US05767281

反応ノート

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