1,2-Dimethoxyethane → HCID 66578609, compound

HRID 1528688Notes

Reaction equation

HRID 1528688 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:14][C:15](=[O:24])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[C:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)([OH:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:13][C:10]1[C:9]([NH:14][C:15](=[O:24])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([C:25]([OH:27])=[O:26])[CH:33]=3)=[CH:3][CH:4]=2)[O:12][N:11]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 66578113HCID 66578113, compound

Product 1

HCID 66578609HCID 66578609, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
88 °C

Procedure

N-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-3-phenyl-propionamide (0.100 g, 0.26 mmol), 3-carboxyphenylboronic acid (0.052 g, 0.31 mmol), tetrakis(triphenylphosphine)palladium(0) (0.030 g, 0.03 mmol), and potassium carbonate (0.072 g, 0.52 mmol) were combined in 2:1 DME:H2O. The mixture was purged with N2 and stirred at 88° C. in a sealed container for 1 hour. After aqueous workup the crude material was purified by preparative HPLC to give the title compound.

Workup

  1. customThe mixture was purged with N2
  2. customAfter aqueous workup the crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-3f42a4aed4f54999a719061c8c1c2fa9
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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