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

HRID 1880074
ノート
印刷プレビュー

反応式

HRID 1880074 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][O:28][CH2:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].I[CH3:32]>CN(C=O)C.O>[O:28]1[CH2:27][CH:26]=[C:25]([C:24]2[C:19]([O:18][C:15]3[CH:14]=[CH:13][C:12]([C:10]([C:2]4[N:3]([CH3:32])[C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[N:1]=4)=[O:11])=[CH:17][CH:16]=3)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:30][CH2:29]1
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 2

HCID 6328Methyl iodideHCID 59327026(1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of (1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone (0.350 g, 0.881 mmol) in DMF (5 mL) was treated with iodomethane (0.083 mL, 1.321 mmol). The mixture was stirred at RT and after 4 hours, it was diluted with water and extracted (2×) with DCM. The organic portions were combined 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, reduced and purified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes to afford (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone as white solid. MS (ESI, pos. ion) m/z: 411.9 (M+1). IC50 (uM) +++++.

後処理

  1. extractionextracted (2×) with DCM
  2. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. 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-c47fb1978b9244ae9b665e914c4818f6
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318718B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート