Phenylboronic Acid → HCID 69259026, compound

HRID 1428982Notes

Reaction equation

HRID 1428982 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C.O.[Cu]I>[CH3:1][C:2]1[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 99200Ethyl 4-methyl-5-imidazolcarboxylate

Product 1

HCID 69259026HCID 69259026, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 19096565Water ethanolSolvent

Procedure

Part A: A magnetically stirred mixture of ethyl 5-methyl-1H-imidazole-4-carboxylate (13.875 g, 0.090 mol), phenylboronic acid (13.16 g, 0.108 mol) and CuI (0.85 g, 0.0045 mol) in ethanol/water (900 ml, 1/1 (v/v)) was divided in 12 equal portions and reacted in parallel at 85° C. for 60 hours. After cooling to room temperature the 12 portions were combined and concentrated in vacuo. The residue was purified by flash chromatography (Ethylacetate/petroleum ether 40-65=1/1 (v/v)) to give ethyl 5-methyl-1-phenyl-1H-imidazole-4-carboxylate (5.88 g, 26% yield). 1H-NMR (400 MHz, CDCl3): 1.42 (t, J=7 Hz, 3H), 2.47 (s, 3H), 4.40 (q, J=7 Hz, 2H), 7.26-7.31 (m 7.56 (m, 3H), 7.59 (s, 1H).

Workup

  1. customreacted in parallel at 85° C. for 60 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (Ethylacetate/petroleum ether 40-65=1/1 (v/v))

Sources & evidence

ORD record
ord-e22b0fa096cb40db9446986854669cac
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

Loading…