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Imidazole → 3-Cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720415
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인쇄 미리보기

반응식

HRID 720415 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].C(=O)([O-])[O-].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 19660Carbonate IonHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

생성물 1

HCID 218921063-Cyano-1-(4-imidazol-1-yl-benzoyl)-pyrrolo[1,2-a]quinoline수율 76.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

A mixture of 3-cyano-(4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline (8 mg, 0.025 mmol), pottasium carbonate (10 mg, 0.072 mmol) and imidazole (5 mg, 0.073 mmol) were heated in 500 μL of DMF overnight. The reaction mixture was cooled to room temperature, diluted with 10 mL of ethyl acetate, washed with water (3×10 mL), saturated NaCl and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated. The crude was purified by chromatography (3% methanol/chloroform) to yield the title compound (6.9 mg, 75%). 1H NMR (CDCl3): 8.21 (dt, J=7.80, 1.20 Hz, 2H), 8.08 (d, J=8.72 Hz, 1H), 8.02 (s, 1H), 7.87 (dd, J=7.81, 1.82 Hz, 1H), 7.73 (m, 2H), 7.60 (m, 4H), 7.46 (s, 1H), 7.42 (t, J=1.24 Hz, 1H), 7.30 (s, 1H).

후처리

  1. washwashed with water (3×10 mL), saturated NaCl
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by chromatography (3% methanol/chloroform)

출처 및 근거

ORD 기록
ord-107b03b101804228b89eaed877375598
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135480B2

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