Potassium Carbonate → HCID 59219269, compound

HRID 2247429Notes

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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21525435Methyl 5-bromo-2-fluorobenzoateHCID 59219096HCID 59219096, compound

Product 1

HCID 59219269HCID 59219269, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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
Patent number
US07687664B2

Reaction notes

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