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

HRID 595569
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HRID 595569 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b0403d28a50743b59dc2e2dddcc349c9
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242998B2

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