Potassium Carbonate → HCID 67212487, compound

HRID 554631Notes

Reaction equation

HRID 554631 reaction equation
[CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]([O:36][C:37](=[O:46])[CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[C:43](Br)[CH:44]=1)[CH3:35].C(=O)([O-])[O-].[K+].[K+]>COCCOC.[NH4+].[Cl-].CCOC(C)=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>[CH2:34]([O:36][C:37](=[O:46])[CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[C:43]([C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:22])[F:23])=[CH:20][C:15]=2[CH2:14][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([CH:11]2[CH2:13][CH2:12]2)=[O:10])[CH:44]=1)[CH3:35]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 67212354HCID 67212354, compound

Product 1

HCID 67212487HCID 67212487, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

Cyclopropanecarboxylic acid benzyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide (60% pure; 1.07 g, 1.4 mmol), (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (0.375 g, 1.5 mmol), and potassium carbonate (0.484 g, 3.5 mmol) were combined in DME (8 mL) and H2O (4 mL), and the solution was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.162 g, 0.14 mmol) was added, and the reaction was stirred at 90° C. overnight. The mixture was diluted with saturated aqueous NH4Cl and EtOAc. The aqueous layer was separated and extracted twice with EtOAc, and the combined organic layers were dried and concentrated. The residue was purified by preparative HPLC to give (5-{2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester, which was then hydrolyzed in the following step, as well as the hydrolyzed product.

Workup

  1. customH2O (4 mL), and the solution was purged with N2 for 15 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted twice with EtOAc
  4. customthe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-06a61b3cd1ea4549b31a79cb6b4094b7
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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