Sodium Iodide → HCID 67973964, compound

HRID 1777659Notes

Reaction equation

HRID 1777659 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][CH:24]=1.ClCCl.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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]>[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][CH2:20][NH:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:25][CH:24]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 67974260HCID 67974260, compound

Product 1

HCID 67973964HCID 67973964, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(furan-2-ylmethyl)benzamide was prepared according to method B with furan-2-yl boronic acid (0.027 g; 0.242 mmol), N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(chloromethyl)benzamide (0.080 g; 0.231 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with dichloromethane (0.018; 0.023 mmol), sodium iodide (0.070 g; 0.461 mmol) and sodium carbonate (0.049 g; 0.461 mmol) in dimethoxyethane (3 mL) and water (1 mL) was irradiated in the microwave at 130° C. for 15 minutes. Flash chromatography on silica gel (eluent 20 to 80% ethyl acetate in heptane) furnished 0.016 g (19%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(furan-2-ylmethyl)benzamide was prepared
  2. customwas irradiated in the microwave at 130° C. for 15 minutes

Sources & evidence

ORD record
ord-b610cbe00cb941e5a11cf159d0c3533e
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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