Sodium Carbonate → HCID 86664550, compound

HRID 513291Notes

Reaction equation

HRID 513291 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[CH:14]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 866645466-Chloro-4-(3-iodobenzylamino)nicotinamide

Product 1

HCID 86664550HCID 86664550, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-4-(3-iodobenzylamino)nicotinamide (200 mg, 0.50 mmol) in Dioxane (2 mL) was added pyridine-4-boronic acid (92 mg, 0.75 mmol) and Pd(PPh3)2Cl2 (56 mg, 0.08 mmol), followed by a solution of Na2CO3 (173 mg, 1.63 mmol) in H2O (1 mL). After stirring at 100° C. for 2 h, it was concentrated and purified by preparative HPLC to give 6-chloro-4-(3-(pyridine-4-yl)benzylamino)nicotinamide (56 mg).

Workup

  1. concentrationit was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d590ac809d10472a96f0261837414f08
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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