Nitrogen → N-(3-(benzofuran-2-yl)-5-nitrophenyl)acetamide

HRID 64129Notes

Reaction equation

HRID 64129 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N#N.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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]>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamideHCID 113685332-(1-Benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 89500178N-(3-(benzofuran-2-yl)-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (2 g, 7.7 mmol) in 1,2-dimethoxyethane (25 ml) was degassed by N2 bubbling for 5 min. 2-(Benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.45 g, 10 mmol, 1.3 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.63 g, 0.77 mmol, 0.1 eq.) and aqueous sodium carbonate (2.45 g, 23.1 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was directly used for the next step.

Workup

  1. customthe mixture was degassed for another 5 min

Sources & evidence

ORD record
ord-1e27b309856a4d778203c36fa0fb4ba4
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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