Sodium Carbonate → HCID 67456175, compound

HRID 643498Notes

Reaction equation

HRID 643498 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=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:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:17])[CH:23]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamate

Product 1

HCID 67456175HCID 67456175, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (4-bromo-benzyl)-carbamic acid tert-butyl ester (600 mg), 3-hydroxybenzeneboronic acid (373 mg), sodium carbonate (333 mg), palladium (II) acetate (10 mg) and tricyclohexylphosphine (13 mg) in water (3.5 ml) and dioxane (14 ml) is kept at 90° C. under micro wave conditions for 230 min. The mixture is cooled down to rt and is filtered through an EXTUBE extraction column with EtOAc (200 ml). The filtrate is evaporated and the resulting crude product is purified on silica (90 g) with cyclohexane/EtOAc 95:5 to 70:30 to afford pure (3′-hydroxy-biphenyl-4-ylmethyl)-carbamic acid tert-butyl ester.

Workup

  1. filtrationis filtered through an EXTUBE extraction column with EtOAc (200 ml)
  2. customThe filtrate is evaporated
  3. customthe resulting crude product is purified on silica (90 g) with cyclohexane/EtOAc 95:5 to 70:30

Sources & evidence

ORD record
ord-f062be62da8d4b0fb702aa3c060dae3c
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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