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Benzonitrile, 4-bromo- → 6-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide

HRID 595569
ノート
印刷プレビュー

反応式

HRID 595569 の反応式
[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12](=[O:15])[NH:13][CH3:14])=[C:7](B(O)O)[O:8][C:4]=2[CH:3]=1.Br[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>O1CCOCC1.O.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]>[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12]([NH:13][CH3:14])=[O:15])=[C:7]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[O:8][C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 12162Benzonitrile, 4-bromo-HCID 90332513(6-Amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid

生成物 1

HCID 903324446-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide収率 26%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 21886435
1,4-Dioxane--water (1/1)
溶媒

実験手順

A solution of (6-amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid (1 g, 3.19 mmol), 4-bromobenzonitrile (1.17 g, 6.39 mmol), K3PO4.3H2O (1.7 g, 6.39 mmol) and Pd(dppf)Cl2 (40 mg) in dioxane/H2O (10 mL/2 mL) was stirred at 80° C. for 4 h. The mixture was filtered to remove the solid and then the mixture was diluted with water and extracted with EA. The organic layer was washed with brine, dried with Na2SO4 and concentrated. The residue was purified by column chromatography (PE:EA=5:1) to give 6-amino-5-bromo-2-(4-cyanophenyl)-N-methylbenzofuran-3-carboxamide (300 mg, yield: 26%). 1H-NMR (CDCl3, 400 MHz) δ 8.09 (d, J=8.0 Hz, 2H), 7.72 (s, 1H), 7.65 (d, J=8.4 Hz, 2H), 6.84 (s, 1H), 5.84 (s, 1H), 4.28 (s, 2H), 3.00 (d, J=4.4 Hz, 3H). MS (M+H)+: 370/372.

後処理

  1. filtrationThe mixture was filtered
  2. customto remove the solid
  3. additionthe mixture was diluted with water
  4. extractionextracted with EA
  5. washThe organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (PE:EA=5:1)

出典と根拠

ORDレコード
ord-b0403d28a50743b59dc2e2dddcc349c9
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242998B2

反応ノート

読み込み中…

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