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Potassium Carbonate → Methyl 3-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)benzoate

HRID 2247432
Notes
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Reaction equation

HRID 2247432 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:19][O:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:8]([O:7][C:6]([NH:5][CH2:4][C:3]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:2]=1[C:27]1[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:21]([O:20][CH3:19])=[O:22])=[O:12])([CH3:11])([CH3:10])[CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 22930485Tert-butyl (2-bromo-5-methoxybenzyl)carbamate

Product 1

HCID 59218922Methyl 3-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)benzoateYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Conditions

Temperature
100 °C

Procedure

1.26 g of t-Butyl N-(2-bromo-5-methoxybenzyl)carbamate, 790 mg of 3-methoxycarbonylphenylboronic acid, 231 mg of tetrakistriphenyl phosphine palladium and 2.20 g of potassium carbonate were dissolved in 25 ml of toluene, and the mixture was heated at 100° C. for 7 hours in a nitrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column, to give 470 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-3d6a6691f918489a885ec7430cfdce98
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07687664B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes