Imidazole → HCID 21934562, 화합물

HRID 1241442노트

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HRID 1241442 반응식
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

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 21934548HCID 21934548, 화합물

생성물 1

HCID 21934562HCID 21934562, 화합물수율 86%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-66bcee5b362b4dd6a6f0b9fe628d5889
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115596B2

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