1,2-Dimethoxyethane → (E)-N,N-Diallyl-4-(2-(4-(benzofuran-2-yl)phenyl)vinylsulfonamido)pyridine-3-sulfonamide

HRID 2283346Notes

Reaction equation

HRID 2283346 reaction equation
[CH2:1]([N:4]([CH2:27][CH:28]=[CH2:29])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]=[C:31]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:1]([N:4]([CH2:27][CH:28]=[CH2:29])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15](/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([C:31]2[O:30][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH:32]=2)=[CH:22][CH:21]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 57751063(E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide

Product 1

HCID 57751062(E)-N,N-Diallyl-4-(2-(4-(benzofuran-2-yl)phenyl)vinylsulfonamido)pyridine-3-sulfonamideYield 38%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide (0.47 g, 0.94 mmol), 2-benzofuranboronic acid (0.20 g, 1.23 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.039 g, 0.050 mmol), cesium carbonate (0.46 g, 1.41 mmol), 1,2-dimethoxyethane (9 mL) and water (1 mL) under an atmosphere of argon was heated at 120° C. for 15 min in a microwave. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 38% yield.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-dac5a752ba8244489d61bc0f2f0a4de4
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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