Sodium Iodide → HCID 67973005, compound

HRID 925403Notes

Reaction equation

HRID 925403 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[N:16]=[N:15][C:14]([C:17]([NH:19][CH2:20][CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([Cl:31])[CH:29]=3)[NH:24][CH:23]=2)=[O:18])=[CH:13][CH:12]=1.[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].C(OCC)(=O)C>[Cl:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:21][CH2:20][NH:19][C:17]([C:14]1[N:15]=[N:16][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:13]=1)=[O:18]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86700713HCID 86700713, compound

Product 1

HCID 67973005HCID 67973005, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of phenylboronic acid (0.022 g; 0.179 mmol), 6-chloro-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyridazine-3-carboxamide (0.050 g; 0.149 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.012 g; 0.015 mmol), sodium iodide (0.044 g; 0.298 mmol) and sodium carbonate (0.032 g; 0.298 mmol) in dimethoxyethane (3 mL) and water (1 mL) was irradiated in the microwave oven at 130° C. for 15 minutes. The resulting solution was reported between water and ethyl acetate and the organic layer was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 20 to 80% ethyl acetate in heptane) to afford 0.0038 g (7%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-6-phenylpyridazine-3-carboxamide as a white solid.

Workup

  1. customwas irradiated in the microwave oven at 130° C. for 15 minutes
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica gel (eluent 20 to 80% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3d07751e171e45819a48a08b3401d8f4
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

Loading…