Potassium Carbonate → HCID 21049421, 화합물

HRID 222051

반응식

HRID 222051 반응식
[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]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 680073-Fluorobenzyl bromide

생성물 2

HCID 21049421HCID 21049421, 화합물수율 37%HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazole수율 32%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ccedf090936f47639c8c200e442da7b6
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207172B2

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