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Potassium Carbonate → Perfluorophenyl 1-(3'-chloro-5'-fluoro-4-methoxy-[1,1'-biphenyl]-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

HRID 1504509
ノート
印刷プレビュー

反応式

HRID 1504509 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([O:21][C:22]4[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=4[F:32])(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:33])[CH:7]=1.[Cl:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[C:41]([F:43])[CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:36][C:37]1[CH:38]=[C:39]([C:2]2[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([N:8]3[C:17]4[C:12](=[CH:13][C:14]([S:18]([O:21][C:22]5[C:23]([F:32])=[C:24]([F:31])[C:25]([F:30])=[C:26]([F:29])[C:27]=5[F:28])(=[O:19])=[O:20])=[CH:15][CH:16]=4)[CH:11]=[CH:10][C:9]3=[O:33])[CH:7]=2)[CH:40]=[C:41]([F:43])[CH:42]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 15391287(3-Chloro-5-fluorophenyl)boronic acidHCID 117736973Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

生成物 1

HCID 117737031Perfluorophenyl 1-(3'-chloro-5'-fluoro-4-methoxy-[1,1'-biphenyl]-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate収率 38.1%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Perfluorophenyl 1-(5-bromo-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (15.00 g, 26.0 mmol), (3-chloro-5-fluorophenyl)boronic acid (4.99 g, 28.6 mmol), potassium carbonate (10.79 g, 78 mmol), and Pd(PPh3)4 (3.01 g, 2.60 mmol) were combined in 1,4-dioxane (98 ml) and water (32.5 ml). The reaction was heated to 90° C. for 2.5 h. After cooling to room temperature, the reaction was diluted with DCM and washed with water. The organics were dried via phase separator and concentrated in vacuo. The crude oil was dry loaded onto silica gel and purified via MPLC, eluting with 0-100% ethyl acetate (with a 10% DCM additive) to yield perfluorophenyl 1-(3′-chloro-5′-fluoro-4-methoxy-[1,1′-biphenyl]-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (6.20 g, 9.91 mmol, 38.1% yield) as a beige solid. m/z (ESI) 626.0 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. customThe organics were dried via phase separator
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was dry
  6. custompurified via MPLC
  7. washeluting with 0-100% ethyl acetate (with a 10% DCM additive)

出典と根拠

ORDレコード
ord-2307a1dccf0c4aaaa4fd6684eb3de743
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09212182B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート