Sodium Iodide → HCID 67974637, compound

HRID 1777660Notes

Reaction equation

HRID 1777660 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][NH:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=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:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][NH:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:26][CH:25]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 67974260HCID 67974260, compound

Product 1

HCID 67974637HCID 67974637, compoundYield 20%

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-(pyridin-3-ylmethyl)benzamide was prepared according to method B with pyridin-3-ylboronic acid (0.029 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 75 to 100% ethyl acetate in heptane) furnished 0.018 g (20%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-bf97388666e24d4187ca1fc97b1a0a02
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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