Sodium Carbonate → HCID 118558226, compound

HRID 2201914Notes

Reaction equation

HRID 2201914 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:27])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.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>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:27])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 728512-(4-Bromophenyl)ethanolHCID 44254049HCID 44254049, compound

Product 1

HCID 118558226HCID 118558226, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid (1.00 g, 4.29 mmol), 2-(4-bromophenyl)ethanol (0.862 g, 4.29 mmol), 2M Na2CO3 (2.145 mL, 4.29 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.149 g, 0.129 mmol) in toluene (3 mL) and MeOH (0.857 mL) was heated at 100° C. under microwave irradiation for 2.5 h. The mixture was extracted with EtOAc, toluene and DCM. The combined organics were concentrated. The residue was purified by column chromatography and recrystallized from EtOAc to give the title compound. LCMS m/z=310.5 [M+H]+.

Workup

  1. extractionThe mixture was extracted with EtOAc, toluene and DCM
  2. concentrationThe combined organics were concentrated
  3. customThe residue was purified by column chromatography
  4. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-45d63fb609f8464da44ab90b20484fc2
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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