Water → HCID 45137193, compound

HRID 2278737Notes

Reaction equation

HRID 2278737 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.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.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:17]=[C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[C:27]([F:38])([F:37])[F:26])[CH:15]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 67304474HCID 67304474, compound

Product 1

HCID 45137193HCID 45137193, 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 (30.00 mg, 0.07589 mmol), 2-(trifluoromethyl)phenylboronic acid (28.83 mg, 0.1518 mmol), cesium carbonate (123.6 mg, 0.3795 mmol), tetra-n-butylammonium iodide (28.03 mg, 0.07589 mmol), and POPd (3.808 mg, 0.007589 mmol) were dissolved in Water (0.06 mL, 3 mmol) and N,N-dimethylformamide (0.3 mL, 4 mmol). The reaction mixture was microwaved for 20 mins at 150 degrees. The reaction was purified directly by reversed phase chromatography.

Workup

  1. customThe reaction mixture was microwaved for 20 mins at 150 degrees
  2. customThe reaction was purified directly by reversed phase chromatography

Sources & evidence

ORD record
ord-f6c914c182de49278ac4d67c1b497b56
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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