Sodium Carbonate → HCID 67318017, compound

HRID 1013791Notes

Reaction equation

HRID 1013791 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)[C:8]2=[O:19])=[C:4]([Cl:22])[CH:3]=1.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1.C(=O)([O-])[O-].[Na+].[Na+]>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.CCOC(C)=O.O>[Cl:22][C:4]1[CH:3]=[C:2]([C:27]2[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=2)[CH:21]=[CH:20][C:5]=1[CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[C:8]1=[O:19]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57671390HCID 57671390, compound

Product 1

HCID 67318017HCID 67318017, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 3-(4-Bromo-2-chloro-benzyl)-1-(4-oxo-cyclohexyl)-pyrrolidin-2-one (0.5, 1.3 mmol), 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.814 g, 3.9 mmol), sodium carbonate (0.689 g, 6.5 mmol) in DME (8 mL)/H2O (3 mL) and degas with a stream of nitrogen. Add (Ph3P)4Pd (0.150 g, 0.13 mmol), and stir at 80° C. for 17 hour under nitrogen atmosphere. Cool to ambient temperature and add ethyl acetate (20 mL) and water (10 mL). Extract the aqueous phase with ethyl acetate (2×20 mL), dry (sodium sulfate) and condense under reduced pressure. Chromatography (silica, EtOAc) yields 0.287 g (42%) as a white solid MS (m/z): 386 (M+1).

Workup

  1. extractionExtract the aqueous phase with ethyl acetate (2×20 mL)
  2. customdry
  3. custom(sodium sulfate) and condense under reduced pressure

Sources & evidence

ORD record
ord-6503df9867724698aeaeaaae1296cf6b
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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