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

HRID 595569
Notes
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Reaction equation

HRID 595569 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b0403d28a50743b59dc2e2dddcc349c9
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242998B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes