Potassium Carbonate → 4,5-Dibromo-1-ethyl-2-(naphthalen-1-yl)-1H-imidazole

HRID 12456Notes

Reaction equation

Br[C:2]1[N:3]([CH2:9][CH3:10])[C:4]([Br:8])=[C:5]([Br:7])[N:6]=1.[C:11]1(OB(C2C=CC=CC=2)O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:7][C:5]1[N:6]=[C:2]([C:19]2[C:20]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[CH:17][CH:18]=2)[N:3]([CH2:9][CH3:10])[C:4]=1[Br:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2,4,5-tribromo-1-ethyl-1H-imidazole (13.19 g, 40 mmol) and 1-naphthylphenylboronic acid (6.88 g, 40 mmol, 1.0 eq.) in toluene (100 ml) is added aqueous potassium carbonate solution (2.0 N, 40 ml, 2.0 eq.), followed by the addition of Pd(PPh3)4 (1.154 g, 1 mmol, 0.025 eq.). The resulting mixture is degassed with nitrogen, and then stirred at 90° C. for 16 hr. After cooling to rt, the reaction mixture is diluted with EtOAc (100 ml), washed with water and brine, and dried over sodium sulfate. After the solvent is removed, the crude product is purified through flash chromatography to afford the title product LCMS 380 (M+1).

Workup

customThe resulting mixture is degassed with nitrogen
temperatureAfter cooling to rt
additionthe reaction mixture is diluted with EtOAc (100 ml)
washwashed with water and brine
dry with materialdried over sodium sulfate
customAfter the solvent is removed
customthe crude product is purified through flash chromatography

Sources & evidence

ORD record: ord-707e734d43db4ad18a4482477ac34ea0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728009B1

Reaction notes

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