Water → HCID 117892049, compound

HRID 930547Notes

Reaction equation

HRID 930547 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=1.[CH3:19][C:20]1(C)[C:24](C)(C)OB(C(C)=C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(COC)OC>[N+:16]([C:5]1[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][C:2]([C:20]([CH3:24])=[CH2:19])=[N:3][CH:4]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 117892050HCID 117892050, compound

Product 1

HCID 117892049HCID 117892049, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-5-nitro-N-(pyridin-2-ylmethyl)pyridin-4-amine E-2.17″ (125 mg; 0.47 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (200 μl; 1.06 mmol), cesium carbonate (300 mg; 0.90 mmol) and [1,1′-Bis[diphenylphosphino]-ferrocene]dichloropalladium (30 mg; 0.04 mmol) are suspended in 7.5 ml dimethoxyethane and 2.5 ml water and heated for 1 h at 100° C. The solvent of the reaction mixture is removed under reduced pressure and the crude product is purified using reversed phase chromatography (Method: prep. HPLC1).

Workup

  1. customThe solvent of the reaction mixture is removed under reduced pressure
  2. customthe crude product is purified

Sources & evidence

ORD record
ord-894345f146cf480289ff0c005c691696
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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