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

HRID 410201
ノート
印刷プレビュー

反応式

HRID 410201 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](Br)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[O:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1.C([O-])(=O)C.[K+].O1CCOCC1>CO.O>[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:29]3[CH2:30][CH2:31][O:26][CH2:27][CH:28]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 59326957(1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone

生成物 1

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

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A clear 150 ml pressure tube was charged with (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone (1.5 g, 3.80 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.959 g, 4.57 mmol), Bis-[4-(di-tert-butylphosphino)-N,N-dimethylbenzenamine]Palladium dichloride (2.69 g, 3.80 mmol), potassium acetate (0.373 g, 3.80 mmol), Dioxane (9 mL) and Water (1.000 mL). The reaction flask was flushed with nitrogen and capped. The reaction was heated to 100° C. for 16 hours. The reaction was then cooled down to RT and partitioned with ethyl acetate (50 ml) and water (50 ml). The organic layer was 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 then filtered. The volatile were reduced to a smaller volume and the solid that precipitated out was filtered off. The cake obtained was suspended in hot MeOH, filtered and dried to give (1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 397.9 (M+1).

後処理

  1. customThe reaction flask was flushed with nitrogen
  2. customcapped
  3. temperatureThe reaction was then cooled down to RT
  4. custompartitioned with ethyl acetate (50 ml) and water (50 ml)
  5. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  6. dry with materialThe organic layer was then dried with sodium sulfate
  7. filtrationfiltered
  8. customthe solid that precipitated out
  9. filtrationwas filtered off
  10. customThe cake obtained
  11. filtrationfiltered
  12. customdried

出典と根拠

ORDレコード
ord-c067d518482f436cb3bb9103ec6bc407
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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