Sodium Carbonate → HCID 78321671, compound

HRID 2201926Notes

Reaction equation

HRID 2201926 reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:31]([OH:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3([C:31]([OH:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 974471-(4-Chlorophenyl)cyclopentanecarboxylic acidHCID 68728719HCID 68728719, compound

Product 1

HCID 78321671HCID 78321671, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (300 mg, 1.113 mmol), 1-(4-chlorophenyl)cyclopentanecarboxylic acid (300 mg, 1.335 mmol), Na2CO3 (472 mg, 4.45 mmol), and dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium (7.88 mg, 0.011 mmol) in 1,4-dioxane (6 mL) and H2O (1.2 mL) was heated under microwave irradiation at 150° C. for 10 min. The mixture was concentrated. The residue was purified by HPLC to give the title compound. LCMS m/z=378.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-d37adb3ab2784494a7200cc829452a94
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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