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Sodium Bicarbonate → N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide

HRID 1641570
ノート
印刷プレビュー

反応式

HRID 1641570 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)=[CH:4][CH:3]=1.[CH:22]([C:24]1[S:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])O.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:22]([C:24]1[S:28][C:27]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]3([NH:18][C:19](=[O:21])[CH3:20])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:26][CH:25]=1)=[O:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27734305-Formyl-2-thiopheneboronic acidHCID 46202882N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

生成物 1

HCID 57624621N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide収率 21.5%

試薬・触媒・溶媒

3
HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixed solution of N-{5-[2-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (1.07 g) of Reference Example 5, 5-formyl-2-thiopheneboronic acid (0.56 g), sodium hydrogen carbonate (1.51 g), palladium(II) acetate (33.7 mg) and 2-(di-t-butylphosphino)biphenyl (89.5 mg) in 1,2-dimethoxyethane (12 mL)-water (4 mL) was stirred at 65° C. for 9 hr under a nitrogen atmosphere. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.25 g) as brown crystals.

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2a17d82e6e78402c8ea7b64e743f3c12
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114902B2

反応ノート

読み込み中…

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