Water → HCID 45137051, compound

HRID 2278735Notes

Reaction equation

HRID 2278735 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:15]=[C:16](Br)[CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.CN(C)C=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:15]=[C:16]([C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)[CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 67304474HCID 67304474, compound

Product 1

HCID 45137051HCID 45137051, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In a 5 mL microwave vial, 5-Bromo-4′-methyl-biphenyl-3-carboxylic acid (6-methyl-pyridin-3-ylmethyl)-amide (20 mg, 0.05 mmol), Pyridine-4-boronic acid (12.44 mg, 0.1012 mmol), cesium carbonate (82.42 mg, 0.2530 mmol), tetra-n-butylammonium iodide (18.69 mg, 0.05060 mmol), and POPd (2.538 mg, 0.005060 mmol) were dissolved in Water (0.04 mL, 2 mmol) and N,N-dimethylformamide (0.2 mL, 2 mmol). The reaction mixture was microwaved for 20 mins at 150 degrees. The reaction was purified directly by reversed phase HPLC (acetonitrile:water gradient) at pH 10. The combined pure fractions were reduced in vacuo to afford the title compound as an off white solid.

Workup

  1. customThe reaction mixture was microwaved for 20 mins at 150 degrees
  2. customThe reaction was purified directly by reversed phase HPLC (acetonitrile:water gradient) at pH 10

Sources & evidence

ORD record
ord-4d13c25bb3894c43b3f2c3a14ed40a34
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

Loading…