Water → HCID 45137633, compound

HRID 2278743Notes

Reaction equation

HRID 2278743 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].[CH3:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.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:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH2:29][O:28][CH3:27])[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 37594082-(Methoxymethyl)benzeneboronic acidHCID 58449363HCID 58449363, compound

Product 1

HCID 45137633HCID 45137633, 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-(methoxymethyl)phenylboronic acid (40.36 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 pH10. 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 pH10

Sources & evidence

ORD record
ord-730a97a122224339bd60af319dbe5464
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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