Diisopropylamine → HCID 11462234、化合物

HRID 2373456ノート

反応式

HRID 2373456 の反応式
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[CH:12])[CH:6]=1)[CH3:2].I[C:15]1[CH:27]=[CH:26][C:18]2[O:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][O:23][C:17]=2[CH:16]=1.C1COCC1.C(NC(C)C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CCCCCC>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][C:15]2[CH:27]=[CH:26][C:18]3[O:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][O:23][C:17]=3[CH:16]=2)[CH:6]=1)[CH3:2]

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 15540684Ethyl 3-ethynylbenzoateHCID 598526917-iodo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine

生成物 1

HCID 11462234HCID 11462234、化合物収率 54.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8058Hexane溶媒

実験手順

To a mixture under N2 of 3-ethynyl-benzoic acid ethyl ester (9) (50 mg), 7-iodo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine (5) (87 mg) (example 1b), [PdCl2(PPh3)2] (10 mg) and copper(I) iodide (5.5 mg) is added a degassed mixture of THF (2.5 ml) and diisopropylamine (2.5 ml). After 5.5 h stirring at RT hexane (15 ml) is added and the mixture is washed with 1 N aq. HCl sol. (2×15 ml), H2O (15 ml) and brine (15 ml). After drying over MgSO4 the solvent is evaporated and the product is purified by flash chromatography (silica gel, hexane/1% AcOEt). 55 mg of 3-(3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-benzoic acid ethyl ester (10) are obtained as a colourless gum, MS (ESI) 350.2 (M•)+.

後処理

  1. additionis added
  2. washthe mixture is washed with 1 N aq. HCl sol. (2×15 ml), H2O (15 ml) and brine (15 ml)
  3. dry with materialAfter drying over MgSO4 the solvent
  4. customis evaporated
  5. customthe product is purified by flash chromatography (silica gel, hexane/1% AcOEt)

出典と根拠

ORDレコード
ord-e90f9d06224345e4a80622f725852989
出典データセット
uspto-grants-2008_12
特許番号
US07459480B2

反応ノート

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