Imidazole → 5-Amino-2-(6-fluoropyridin-3-yl)-6-nitroisoindoline-1,3-dione

HRID 69347

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HRID 69347 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].[F:16][C:17]1[N:22]=[CH:21][C:20](N)=[CH:19][CH:18]=1.N1C=CN=C1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[N:6]([C:20]1[CH:21]=[N:22][C:17]([F:16])=[CH:18][CH:19]=1)[C:5]2=[O:15]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 8194405-Amino-2-fluoropyridineHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 666871515-Amino-2-(6-fluoropyridin-3-yl)-6-nitroisoindoline-1,3-dione수율 12.7%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
200 °C

실험 절차

5-Amino-6-nitroisoindoline-1,3-dione (2.00 g, 9.66 mmol), 6-fluoropyridin-3-amine (3.25 g, 28.98 mmol) and imidazole (1.32 g, 19.32 mmol) were suspended in diphenyl ether (50 mL). The mixture was stirred and heated to 200° C. for 24 h under argon. Then, the solid was filtered, washed with hexanes and purified by column chromatography (silica-gel, CH2Cl2/Acetone=7/3 v/v) to give a yellow solid product, 0.37 g, 12.7% yield. MS: 300.8 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.47 (s, 2H), 8.45 (s, 1H), 8.13-8.06 (m, 1H), 8.34 (d, 1H, J=2.1 Hz), 7.56 (s, 1H), 7.41 (dd, 1H, J1=8.7 Hz, J2=3.0 Hz).

후처리

  1. filtrationThen, the solid was filtered
  2. washwashed with hexanes
  3. custompurified by column chromatography (silica-gel, CH2Cl2/Acetone=7/3 v/v)
  4. customto give a yellow solid product, 0.37 g, 12.7% yield

출처 및 근거

ORD 기록
ord-d011ab5cde6d449083a8c9e244904952
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822500B2

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