Sodium Carbonate → HCID 59278683, compound

HRID 1942909Notes

Reaction equation

HRID 1942909 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]4)=[C:13]([O:23][CH3:24])[CH:12]=3)[N:3]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86640783(4-Chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

Product 1

HCID 59278683HCID 59278683, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (4-chloro-6-methoxy-[1,3,5]triazin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (150 mg, 0.43 mmol), 4-fluorobenzeneboronic acid (67 mg, 0.48 mmol), tetrakis-(triphenylphosphin)-palladium (20 mg, 0.02 mmol) and sodium carbonate (92 mg, 0.87 mmol) in 3 ml of dioxane was refluxed overnight. The mixture was diluted with water, extracted with ethyl acetate and purified by chromatography on silica gel using ethyl acetate as an eluent to give the title compound as a colorless solid (84 mg, yield=47%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-e856de9129e446bdbd4c62afcb5ff316
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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