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

HRID 1372851
ノート
印刷プレビュー

反応式

HRID 1372851 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.[Cu]I>[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

8

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 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 8857Ethyl 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), CuI (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 (DCl/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-27942f942ac84a1a81a07194d9cb60d2
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07160876B2

反応ノート

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