Sodium Carbonate → HCID 58985262, compound

HRID 1157178Notes

Reaction equation

HRID 1157178 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 11824027Tert-butyl 4-(4-bromophenyl)piperazine-1-carboxylate

Product 1

HCID 58985262HCID 58985262, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

4-(4-Bromo-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.171 g, 0.5 mmol), Na2CO3 (0.16 g, 1.5 mmol), 4-fluoro phenyl boronic acid (0.21 g, 1.5 mmol) and (PPh3)2PdCl2 (0.035 g, 0.05 mmol) were mixed in a mixture of THF/H2O (4:1, 7.5 mL) and heated at 70° C. overnight. After cooling to rt, the reaction mixture was partitioned between 50 mL ethyl acetate and 25 mL sat. NaCl solution. The separated organic layer washed with brine (10 mL), dried (MgSO4) and concentrated. The crude was purified with prep TLC (15% ethyl acetate in hexanes) to give a solid (0.071 g). M+H 356.

Workup

  1. temperatureAfter cooling to rt
  2. customthe reaction mixture was partitioned between 50 mL ethyl acetate and 25 mL sat. NaCl solution
  3. washThe separated organic layer washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude was purified with prep TLC (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2cb9fc2148f84de6a1e082ec0cae415e
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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