Sodium Carbonate → HCID 68578938, compound

HRID 643506Notes

Reaction equation

HRID 643506 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[OH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:18])[CH:24]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68578938HCID 68578938, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of [2-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg), 3-hydroxybenzeneboronic acid (296 mg), sodium carbonate (265 mg), palladium (II) acetate (7 mg) and tricyclohexylphosphine (10 mg) in water (3 ml) and dioxane (12 ml) is kept at 90° C. under micro wave conditions for 180 min. The mixture is cooled down to rt and is filtered through an EXTUBE extraction column (Varian) with EtOAc (200 ml). The filtrate is evaporated and the resulting crude product is purified on silica (150 g) with cyclohexane/EtOAc 5/1 to afford pure [2-(3′-hydroxy-biphenyl-4-yl)-ethyl]-carbamic acid tert-butyl ester.

Workup

  1. filtrationis filtered through an EXTUBE extraction column (Varian) with EtOAc (200 ml)
  2. customThe filtrate is evaporated
  3. customthe resulting crude product is purified on silica (150 g) with cyclohexane/EtOAc 5/1

Sources & evidence

ORD record
ord-62874e7a10fd4e0c8e2377faaf3a635e
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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