Sodium Iodide → HCID 86699433, compound

HRID 1777656Notes

Reaction equation

HRID 1777656 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.[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.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:25]2[O:24][CH:28]=[CH:27][CH:26]=2)[CH:16]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 67974165N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide

Product 1

HCID 86699433HCID 86699433, compoundYield 32.1%

Reagents, catalysts & solvents 3

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

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-(furan-2-ylmethyl)benzamide was prepared according to method B with N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-(chloromethyl)benzamide (0.080 g; 0.230 mmol), furan-2-ylboronic acid (0.027 g; 0.241 mmol), tetrakis(triphenylphosphine)palladium (0.027 g; 0.023 mmol), sodium carbonate (0.049 g; 0.461 mmol), sodium iodide (0.069 g; 0.461 mmol), in dimethoxyethane (3 mL) and water (1 mL), irradiated in a microwave oven at 130° C. for 15 minutes. Flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) furnished 0.028 g (32%) of the title compound as a white solid.

Workup

  1. customN-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-(furan-2-ylmethyl)benzamide was prepared

Sources & evidence

ORD record
ord-5e0a08be62ea4b7f805b6e90dd7a7e8a
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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