Benzyl Bromide → 2-Benzyl-6-bromo-2H-indazole

HRID 1850039

反応式

HRID 1850039 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>O1CCOCC1>[CH2:11]([N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[C:2]([Br:1])[CH:3]=[CH:4]2)=[N:8]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 178424716-Bromo-1H-indazole

生成物 1

HCID 585296892-Benzyl-6-bromo-2H-indazole

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

6-Bromoindazole (3.63 g, 18 mmol) was suspended in dioxane (15 mL) and benzyl bromide (2.65 mL, 22 mmol, 1.2 eq.) was added. The reaction was heated to reflux overnight, then allowed to cool to 80° C. after which point ethyl acetate (50 mL) added. The cake was broken up with a spatula and after stirring for 20 min, the solids were filtered off and washed with ethyl acetate, giving glossy white crystals of the hydrobromide salt of 2-benzyl-6-bromoindazole. These were suspended in ethyl acetate (100 mL) and shaken with saturated NaHCO3 (150 mL) until dissolution. The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were concentrated to an off-white powder which was recrystallized from 66% ethanol (40 mL). Washing with water and drying in vacuo gave 2-benzyl-6-bromoindazole (3.30 g, 62%) as shiny white plates.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. additionadded
  4. filtrationthe solids were filtered off
  5. washwashed with ethyl acetate

出典と根拠

ORDレコード
ord-9f201dd0cce546afaab84d6a390c9720
出典データセット
uspto-grants-2015_02
特許番号
US08957049B2

関連ノート

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