Sodium Iodide → HCID 71458475, compound

HRID 1777650Notes

Reaction equation

HRID 1777650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Cl)[CH:16]=1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[N:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:27]2[CH:28]=[N:29][CH:30]=[C:25]([F:24])[CH:26]=2)[CH:16]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 67974165N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide

Product 1

HCID 71458475HCID 71458475, compoundYield 3.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-((5-fluoropyridin-3-yl)methyl)benzamide was prepared according to method B N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide (0.156 g; 0.449 mmol), 5-fluoropyridin-3-ylboronic acid (0.071 g; 0.494 mmol), tetrakis(triphenylphosphine)palladium(0) (0.026 g; 0.022 mmol), sodium carbonate (0.095 g; 0.898 mmol), sodium iodide (0.204 g; 1.35 mmol), in dimethoxyethane (3 mL) and water (1 mL), irradiated in a microwave oven at 130° C. for 15 minutes. Purification by preparative TLC on silica gel (eluent 50% ethyl acetate in heptane) furnished 0.006 g (3%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-((5-fluoropyridin-3-yl)methyl)benzamide was prepared
  2. customPurification by preparative TLC on silica gel (eluent 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-76c205f7653a4700bddd604ef0be722d
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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