2-tert-Butyl-1,1,3,3-tetramethylguanidine → 3-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole

HRID 706701노트

반응식

HRID 706701 반응식
C(N=C(N(C)C)N(C)C)(C)(C)C.[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[NH:16][N:15]=1.Br.Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>CC#N.O>[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[N:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:15]=1

참가 물질

6

반응물 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 129138592-(2-Bromoethyl)pyridine hydrobromideHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 679763233-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole수율 34%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

2-Tert-butyl-1,1,3,3-tetramethyl-guanidine (0.48 mL, 2.4 mmol) was added to a mixture of 3-iodo-4-nitro-1H-indazole (0.30 g, 1.0 mmol) and 2-(2-bromoethyl)pyridine hydrobromide (0.30 g, 1.1 mmol) in CH3CN (4 mL). The mixture was stirred at ambient temperature overnight, diluted with H2O (35 mL), stirred for 30 minutes, and then extracted with CHCl3. The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with EtOAc, to provide 3-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole (0.14 mg, 34%) as a solid.

후처리

  1. stirringstirred for 30 minutes
  2. extractionextracted with CHCl3
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-3518179b6d084d8aae756dee8c6b6544
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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