Potassium Carbonate → HCID 21049421、化合物

HRID 222051

反応式

HRID 222051 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=1)[N:8]=[CH:7]2)([O-:3])=[O:2].[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=3)[N:9]=2)[CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 680073-Fluorobenzyl bromide

生成物 2

HCID 21049421HCID 21049421、化合物収率 37%HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazole収率 32%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

5-nitroindazole (15 g, 92 mmol, 1 eq), 3-fluorobenzylbromide (14.7 mL, 119.5 mmol, 1.3 eq) and potassium carbonate 25.4 g (184 mmol, 2 equiv) were suspended in 150 mL acetonitrile. The reaction mixture was stirred at 70° C. for 12 h, and then allowed to cool to rt. The resultant solid was filtered and washed with CH2Cl2, and the filtrate concentrated in vacuo. The crude mixture of regioisomeric products was purified by column chromatography (5:1 to 4:1 Hex/EtOAc), yielding 5-nitro-1-N-(3-fluorobenzyl)indazole (7.9 g, 32%) and 5-nitro-2-N-(3-fluorobenzyl)indazole (9.2 g, 37%) as yellow solids.

後処理

  1. temperatureto cool to rt
  2. filtrationThe resultant solid was filtered
  3. washwashed with CH2Cl2
  4. concentrationthe filtrate concentrated in vacuo
  5. additionThe crude mixture of regioisomeric products
  6. customwas purified by column chromatography (5:1 to 4:1 Hex/EtOAc)

出典と根拠

ORDレコード
ord-ccedf090936f47639c8c200e442da7b6
出典データセット
uspto-grants-2012_06
特許番号
US08207172B2

関連ノート

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