Imidazole → HCID 21934562、化合物

HRID 1241442ノート

反応式

HRID 1241442 の反応式
O[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:12]([CH3:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:8]=2[N:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:46]I>CCOCC.CC#N>[I:46][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:12]([CH3:13])[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:8]=2[N:21]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 21934548HCID 21934548、化合物

生成物 1

HCID 21934562HCID 21934562、化合物収率 86%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

The mixture of tert-butyl 6-(2-hydroxyethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate (5.6 g, 19.09 mmol), triphenylphosphine (6.51 g, 24.82 mmol), imidazole (1.82 g, 26.72 mmol), and a mixture of CH3CN and dry ether (1:1) was cooled to 0° C. Iodine (6.78 g, 26.72 mmol) was slowly added. The resulting mixture was stirred for 2 hour and then ether (150 mL) was added, washed successively with saturated aqueous Na2S2O3 and brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (silica, 20% EtOAC/Hex) to afford a yellow solid (6.6 g, 86% yield). H NMR (CDCl3) δ 1.55 (s, 9H), 2.93 (s, 3H), 3.18 (t, 2H), 3.30 (t, 2H), 3.458(t, 2H), 3.85 (t, 2H), 6.85(q, 2H). LC-MS (M+H) 404.

後処理

  1. washwashed successively with saturated aqueous Na2S2O3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (silica, 20% EtOAC/Hex)

出典と根拠

ORDレコード
ord-66bcee5b362b4dd6a6f0b9fe628d5889
出典データセット
uspto-grants-2006_10
特許番号
US07115596B2

反応ノート

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