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Potassium Carbonate → Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-hydroxyphenyl)-6-fluorobenzoate

HRID 2247429
Notes
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Reaction equation

HRID 2247429 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Br[C:27]1[CH:28]=[C:29]([C:34]([F:37])=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[C:8]([O:7][C:6]([NH:5][CH2:4][C:3]1[CH:13]=[C:14]([C:27]2[CH:28]=[C:29]([C:34]([F:37])=[CH:35][CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:15]=[CH:16][C:2]=1[OH:1])=[O:12])([CH3:9])([CH3:10])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21525435Methyl 5-bromo-2-fluorobenzoateHCID 59219096Tert-butyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate

Product 1

HCID 59219269Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-hydroxyphenyl)-6-fluorobenzoateYield 72.6%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Conditions

Temperature
80 °C

Procedure

501 mg of t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate, 370 mg of methyl 3-bromo-6-fluorobenzoate, 80 mg of dichlorobistriphenyl phosphinoferrocene palladium and 500 mg of potassium carbonate were dissolved in 8 ml of dimethoxyethane and stirred overnight at 80° C. 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 391 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-4fa81894aa564085b69c9812e2870bc8
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