Water → HCID 45137191, compound

HRID 2278736Notes

Reaction equation

HRID 2278736 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].O.[CH3:33][N:34]([CH3:37])[CH:35]=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][C:12]1[N:11]=[CH:10][C:9]([CH2:8][NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:2]3[CH:3]=[CH:4][CH:16]=[CH:17][C:18]=3[CH2:35][N:34]([CH3:37])[CH3:33])[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:16]=2)=[O:6])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 67304388HCID 67304388, compound

Product 1

HCID 45137191HCID 45137191, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In a 5 mL microwave vial, 3-bromo-5-(5-methylpyridin-2-yl)-N-((6-methylpyridin-3-yl)methyl)benzamide (15.00 mg, 0.03785 mmol), Unnamed (13.55 mg, 0.07570 mmol), cesium carbonate (61.66 mg, 0.1892 mmol), tetra-n-butylammonium iodide (13.98 mg, 0.03785 mmol), and POPd (1.899 mg, 0.003785 mmol) were dissolved in Water (0.03 mL, 2 mmol) and N,N-dimethylformamide (0.1 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 a colorless oil.

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-dc52f35c94b74588a7c9297057c106ef
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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