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(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone → (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

HRID 410208
ノート
印刷プレビュー

反応式

HRID 410208 の反応式
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([C:22]4[N:26]([CH3:27])[C:25]5[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=5[N:23]=4)=[O:21])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C1COCC1.[OH-].[OH-].[Pd+2].[O-2].[O-2].[Mn+4]>[CH3:27][N:26]1[C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[N:23]=[C:22]1[C:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][C:8]2[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:19][CH:18]=1)=[O:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 59326995(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

生成物 1

HCID 59326816(1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 178418406HCID 178418406、化合物触媒HCID 8028Tetrahydrofuran
溶媒

実験手順

A solution of (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone (0.120 g, 0.292 mmol) in THF (10 mL) was evacuated and treated with Pd(OH)2 (20 mg) under nitrogen. The reaction was stirred under a hydrogen atmosphere with a balloon. After 24 hours, the reaction was filtered through a small plug of celite and the filtrate was treated with manganese dioxide (0.254 g, 2.92 mmol). The reaction was stirred at 50° C. for 1 hour and filtered through celite. The filtered was reduced under vacuum. The residue was taken up in DCM and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes to give (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone as a white solid. MS (ESI, pos. ion) m/z: 414.0. IC50 (uM) +++++.

後処理

  1. filtrationthe reaction was filtered through a small plug of celite
  2. stirringThe reaction was stirred at 50° C. for 1 hour
  3. filtrationfiltered through celite
  4. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. custompurified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes

出典と根拠

ORDレコード
ord-551dbdc101074b8dbec7931746da209f
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08759532B2

反応ノート

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