Potassium Carbonate → (3-{3-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-5-methyl-pyridin-2-yl}-4-methoxy-phenyl)-acetic acid ethyl ester

HRID 389267Notes

Reaction equation

HRID 389267 reaction equation
Cl[C:2]1[C:7]([CH2:8][N:9]([CH2:15][CH3:16])[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:6][C:5]([CH3:17])=[CH:4][N:3]=1.[CH2:18]([O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[CH2:18]([O:20][C:21](=[O:40])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:2]2[C:7]([CH2:8][N:9]([C:10]([CH:12]3[CH2:14][CH2:13]3)=[O:11])[CH2:15][CH3:16])=[CH:6][C:5]([CH3:17])=[CH:4][N:3]=2)[CH:24]=1)[CH3:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 58120060[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl esterHCID 58579965Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide

Product 1

HCID 58579952(3-{3-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-5-methyl-pyridin-2-yl}-4-methoxy-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopropanecarboxylic acid (2-chloro-5-methyl-pyridin-3-ylmethyl)-ethyl-amide (0.120 g, 0.48 mmol), [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (0.183 g, 0.57 mmol), and potassium carbonate (0.198 g, 1.43 mmol) were combined in DME and H2O. The mixture was purged with N2 for 10 minutes, and then tetrakis(triphenylphosphine)palladium(0) (0.055 g, 0.05 mmol) was added, and the reaction was stirred at 80° C. for 2 hours. Once no starting material was seen by analytical tlc, the mixture was diluted with H2O and extracted three times with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, decanted, and concentrated, and the residue was purified by silica gel chromatography (0-70% EtOAc in hexanes) to give the title compound.

Workup

  1. customThe mixture was purged with N2 for 10 minutes
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-98893c6c89b84940ac37f893f489ec15
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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