Hydrochloric Acid → HCID 66751287, compound

HRID 535025

Reaction equation

HRID 535025 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][C:41]([OH:43])=[O:42])=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCCC1.C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][C:41]([OH:43])=[O:42])=[CH:36][CH:35]=3)=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1)([CH3:25])([CH3:24])[CH3:23]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 37190022-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic AcidHCID 66750884HCID 66750884, compound

Product 1

HCID 66751287HCID 66751287, compoundYield 26.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-[(4-bromophenyl)carbonyl]-4-(2-tert-butylphenyl)piperazine (1.0 g, 2.49 mmol), [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetic acid (0.653 g, 2.49 mmol), 2 M sodium carbonate solution (3 mL, 6.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.150 g, 0.13 mmol) in tetrahydrofuran (5 mL) and toluene (20 mL) was stirred at 120° C. for 16 h. 6 M hydrochloric acid solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a solid. The solid was dissolved in ethanol-ethyl acetate and recrystallized to obtain a solid (0.3 g, 26%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a solid
  7. customrecrystallized

Sources & evidence

ORD record
ord-728f5dec0c8547e88c4584c694190c2e
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Linked notes

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