Water → HCID 45137194, compound

HRID 2278738Notes

Reaction equation

HRID 2278738 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)[CH:19]=1)[C:5]([NH:7][C@@H:8]([C:10]1[CH:11]=[N:12][C:13]([CH3:16])=[N:14][CH:15]=1)[CH3:9])=[O:6].[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)#[N:28].C(=O)([O-])[O-].[Cs+].[Cs+].O.CN(C)C=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:16][C:13]1[N:12]=[CH:11][C:10]([C@H:8]([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[C:27]#[N:28])[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:17]=2)=[O:6])[CH3:9])=[CH:15][N:14]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27346102-Cyanophenylboronic acidHCID 58449363HCID 58449363, compound

Product 1

HCID 45137194HCID 45137194, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In a 5 mL microwave vial, (R)-3-bromo-5-(5-methylpyridin-2-yl)-N-(1-(2-methylpyrimidin-5-yl)ethyl)benzamide (50.00 mg, 0.1216 mmol), 2-cyanophenylboronic acid (35.72 mg, 0.2431 mmol), cesium carbonate (198.0 mg, 0.6078 mmol), tetra-n-butylammonium iodide (44.90 mg, 0.1216 mmol), and POPd (6.100 mg, 0.01216 mmol) were dissolved in Water (0.09 mL, 5 mmol) and N,N-dimethylformamide (0.4 mL, 6 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 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-9af71c99496b4907b2a9b036fcf88fdc
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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