Potassium Carbonate → HCID 78321360, compound

HRID 2201945Notes

Reaction equation

HRID 2201945 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.Br[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2527324-(4-Bromophenyl)butyric AcidHCID 68728719HCID 68728719, compound

Product 1

HCID 78321360HCID 78321360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

In a microwave reaction vial was placed (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (50 mg, 0.185 mmol), 4-(4-bromophenyl)butanoic acid (49.6 mg, 0.204 mmol), dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium (2.63 mg, 3.71 μmol), and K2CO3 (51.3 mg, 0.371 mmol) in toluene (1.2 mL) and H2O (0.2 mL). The reaction was heated at 130° C. for 120 min under microwave irradiation. The aqueous layer was collected, acidified with 1M HCl, and purified by HPLC to give the title compound. LCMS m/z=352.4 [M+H]+; 1.26 (d, J=6.8 Hz, 0.4H), 1.46 (d, J=6.5 Hz, 2.6H), 1.70-1.82 (m, 1H), 1.87-1.94 (m, 2H), 2.01-2.10 (m, 2H), 2.21-2.30 (m, 1H), 2.33 (t, J=7.4 Hz, 2H), 2.70 (t, J=7.7 Hz, 2H), 3.06-3.18 (m, 4H), 3.35-3.45 (m, 1H), 3.50-3.60 (m, 1H), 3.74-3.84 (m, 1H), 7.31 (d, J=8.3 Hz, 2H), 7.38 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.3 Hz, 2H).

Workup

  1. customIn a microwave reaction
  2. customThe aqueous layer was collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-827aee0677cc4138b75396f704ef98b1
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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