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

HRID 12456ノート

反応式

HRID 12456 の反応式
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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 1811202,4,5-Tribromo-1-ethyl-1H-imidazoleHCID 686301861-Naphthylphenylboronic acid

生成物 1

HCID 534259994,5-Dibromo-1-ethyl-2-(naphthalen-1-yl)-1H-imidazole

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-707e734d43db4ad18a4482477ac34ea0
出典データセット
uspto-grants-2010_06
特許番号
US07728009B1

反応ノート

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