Sodium Carbonate → HCID 86723264、化合物

HRID 1846042ノート

反応式

HRID 1846042 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:16][C:15]=1[F:25].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].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.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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:16][C:15]=2[F:25])[CH:7]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 67280287HCID 67280287、化合物

生成物 1

HCID 86723264HCID 86723264、化合物収率 90%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of (5-chloro-2-methoxyphenyl)boronic acid (714 mg, 1.68 mmol) in dioxane (5 mL) and water (1 mL) was added 1-bromo-4-(ethylsulfonyl)-2-fluorobenzene (Preparation 19, 450 mg, 1.68 mmol), and sodium carbonate (534 mg, 5.04 mmol). The reaction was degassed and then tetrakis(triphenylphosphine) palladium(0) (194 mg, 0.17 mmol) was added and the reaction mixture further degassed. The reaction was placed on a preheated hot plate (110° C.) for 16 hours. The reaction mixture was cooled to room temperature and filtered through celite and the solvent removed in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc:cyclohexane 40:60 to give the title compound as a brown oil in 90% yield, 500 mg.

後処理

  1. customThe reaction was degassed
  2. filtrationfiltered through celite
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with EtOAc:cyclohexane 40:60

出典と根拠

ORDレコード
ord-7ba6c8a2a0f04c3eabbadeee4725166b
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

読み込み中…