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Ethyl Acetate → (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554621
Notes
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Reaction equation

HRID 554621 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10](Br)[CH:11]=1)[CH3:2].[CH2:15]([N:17]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1)[C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>COCCOC.[Cl-].[Na+].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.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10]([C:25]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:24]=2[CH2:23][N:17]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])[CH2:15][CH3:16])[CH:11]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58565131HCID 58565131, compoundHCID 66607375Cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide

Product 1

HCID 86640538(6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

(5-Bromo-6-chloro-pyridin-3-yl)-acetic acid ethyl ester (0.549 g, 1.97 mmol), cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide (0.787 g, 1.97 mmol), and potassium carbonate (0.824 g, 5.91 mmol) were combined in DME (6 mL) and H2O (3 mL), and the solution was purged with N2 for 40 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.338 g, 0.20 mmol) was added, and the reaction was stirred at 85° C. for 2 hours. After cooling to room temperature, the mixture was worked-up with EtOAc, H2O, and brine, and the organic layer was separated, dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester.

Workup

  1. customH2O (3 mL), and the solution was purged with N2 for 40 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0033d9b8852848f6969734e31e3cbacd
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08049015B2

Reaction notes

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