Water → HCID 117892035, compound

HRID 930542Notes

Reaction equation

HRID 930542 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([CH:15]=1)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.CC1(C)C(C)(C)OB([C:27]2[CH2:28][CH2:29][O:30][CH2:31][CH:32]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(COC)OC>[O:30]1[CH2:29][CH:28]=[C:27]([C:2]2[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([CH:15]=2)[NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 24902984HCID 24902984, compound

Product 1

HCID 117892035HCID 117892035, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5-bromo-2-nitro-N-(pyridin-2-ylmethyl)aniline E-1.9″ (145 mg; 0.47 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (145 mg; 0.69 mmol), cesium carbonate (300 mg; 0.90 mmol) and [1,1′-Bis[diphenylphosphino]-ferrocene]dichloropalladium (30 mg; 0.04 mmol) are suspended in 2.5 ml dimethoxyethane and 0.8 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-31711c2bc8944ae8bad14f22318804a5
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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