Nitrogen → 6-(n-butyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897207

反応式

HRID 897207 の反応式
N#N.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.[Br-].[CH2:32]([Zn+])[CH2:33][CH2:34][CH3:35]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH2:32]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][CH2:17]1)[CH2:33][CH2:34][CH3:35]

参加物

7

反応物 3

HCID 947NitrogenHCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 178448256HCID 178448256、化合物

生成物 1

HCID 737123536-(n-butyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One収率 13%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
160 °C

実験手順

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (˜5 mol %), and CuI (˜6 mol %) in dry THF (0.5 mL) followed by n-butyl zinc bromide (0.273 mL, 0.138 mmol (0.5M in THF)) dropwise. The solution was heated in the microwave for 10 minutes at 160° C., filtered, and was purified by Prep HPLC to give 2.5 mg (10%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 417 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm. 96 (t, 3H), 1.33-1.42 (m, 2H), 1.61-1.69 (m, 2H), 1.91-2.03 (m, 2H), 2.41 (br d, 2H), 2.72 (t, 2H), 3.24 (br t, 2H), 3.73 (br d, 2H), 3.96 (m, 3H), 5.42 (s, 1H), 6.30-6.40 (m, 1H), 6.95 (d, 1H), 7.23-7.54 (m, 8H), 7.86 (d, 1H).

後処理

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

出典と根拠

ORDレコード
ord-9a8152a22343432796c7d16df1b85271
出典データセット
uspto-grants-2005_07
特許番号
US06921821B2

関連ノート

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