Sodium Carbonate → 4-(4-Aminophenyl)isoindolin-1-one

HRID 1247445ノート

反応式

HRID 1247445 の反応式
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11].CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[NH2:24][C:23]1[CH:25]=[CH:26][C:20]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][NH:5][C:6]3=[O:11])=[CH:21][CH:22]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 219075094-Bromoisoindolin-1-one

生成物 1

HCID 219075114-(4-Aminophenyl)isoindolin-1-one収率 59.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

A suspension of Example 1C (2 g, 9.43 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)aniline (2.5 g, 11.3 mmol), and Na2CO3 (2.2 g, 20.8 mmol) in DME (68 mL) and water (17 mL) was purged with nitrogen, treated with Pd(PPh3)4 (1 g, 0.9 mmol), and stirred at 90° C. for 19 hours. The reaction mixture was cooled to room temperature, concentrated to one-third its original volume, diluted with ethyl acetate (30 mL) and water (20 mL), and filtered. The filter cake was washed with water and ethyl acetate and dried to give 1.25 g of the desired product. MS (ESI(+)) m/e 225 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to one-third its original volume
  3. additiondiluted with ethyl acetate (30 mL) and water (20 mL)
  4. filtrationfiltered
  5. washThe filter cake was washed with water and ethyl acetate
  6. customdried

出典と根拠

ORDレコード
ord-87b529d2005243cfbdf445e422b4fe49
出典データセット
uspto-grants-2006_10
特許番号
US07129260B2

反応ノート

読み込み中…