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Triphenylphosphine → 2-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole

HRID 2242830
ノート
印刷プレビュー

反応式

HRID 2242830 の反応式
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH:8]2[CH:13]3[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:5][CH:4]=1)#[CH:2].FC(F)(F)C([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1I)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O>[N:10]12[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11]1)[CH:8]([O:7][C:6]1[CH:16]=[CH:17][C:3]([C:1]3[NH:22][C:23]4[C:28]([CH:2]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:4][CH:5]=1)[CH2:9]2
参加物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 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 15346132,2,2-trifluoro-N-(2-iodophenyl)acetamideHCID 210726033-(4-Ethynylphenoxy)quinuclidine

生成物 1

HCID 114839822-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-1H-indole

試薬・触媒・溶媒 2

HCID 8857
Ethyl Acetate
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

Under N2, the mixture of product from Example 6A (114 mg, 0.5 mmol), the product from Example 6B (157 mg, 0.5 mmol), Cul (Strem Chemicals, 14 mg, 0.075 mmol), PPh3 (Aldrich, 39 mg, 0.15 mmol) and K3PO4 (212 mg, 1 mmol) in dioxane (5 mL) was stirred at 80° C. for 20 h. After the reaction was complete, it was diluted with EtOAc (30 mL) and washed with brine (2×5 mL). The organic solution was concentrated under reduced pressure and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3 H2O, 90:10:1, Rf. 0.30) as solid (70 mg, yield, 44%). 1H NMR (300 MHz, CD3OD) δ 1.45-1.59 (m, 1H), 1.65-1.91 (m, 2H), 2.00-2.14 (m, 1H), 2.17-2.24 (m, 1H), 2.75-3.01 (m, 5H), 3.31-3.42 (m, 1H), 4.54-4.62 (m, 1H), 6.66 (d, J=0.7 Hz, 1H), 6.93-7.00 (m, 3H), 7.01-7.08 (m, 1H), 7.35 (dq, J=8.2, 1.0 Hz, 1H), 7.48 (dq, J=7.8, 0.7 Hz, 1H), 7.71 (dt, J=8.8, 2.6 Hz, 2H) ppm. MS (DCI/NH3): m/z 319 (M+H)+.

後処理

  1. washwashed with brine (2×5 mL)
  2. concentrationThe organic solution was concentrated under reduced pressure
  3. customthe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3 H2O, 90:10:1, Rf. 0.30) as solid (70 mg, yield, 44%)

出典と根拠

ORDレコード
ord-aeb2115a882c4993932a818955def7e2
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07674794B2

反応ノート

読み込み中…

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