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Cesium carbonate → 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone

HRID 1880112
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HRID 1880112 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)=[O:17].F[C:26]1[C:31]([CH:32]2[CH2:38][CH2:37][CH2:36][C:35](=[O:39])[CH2:34][CH2:33]2)=[CH:30][CH:29]=[CH:28][N:27]=1>CN1C(=O)CCC1>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:26]2[C:31]([CH:32]3[CH2:38][CH2:37][CH2:36][C:35](=[O:39])[CH2:34][CH2:33]3)=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:20][CH:19]=1)=[O:17]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanoneHCID 593271094-(2-Fluoropyridin-3-yl)cycloheptanone

생성물 1

HCID 593269804-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
140 °C

실험 절차

A mixture of cesium carbonate (0.34 g, 1.03 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.25 g, 1.03 mmol), and 4-(2-fluoropyridin-3-yl)cycloheptanone (0.071 g, 0.343 mmol) in NMP (0.3 mL) under argon was heated to 140° C. for 36 h, then cooled to room temperature. The resulting mixture was partitioned between ethyl acetate and water, the layers were separated, and the organic layer was washed 1N aqueous sodium hydroxide (2×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The oil was purified by silica gel chromatography to give 4-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cycloheptanone. MS (ESI, pos. ion) m/z: 426.1 (M+1). IC50 (uM) +++++.

후처리

  1. temperaturecooled to room temperature
  2. customThe resulting mixture was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. washthe organic layer was washed 1N aqueous sodium hydroxide (2×), saturated aqueous sodium chloride (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe oil was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-d8b53125fa964464817b4e8a6bbfb742
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318718B2

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