Tributylphosphine → Methyl 2-({5-[3-(2-pyridylamino)propoxy]indolyl}methyl)pentanoate

HRID 1295119노트

반응식

HRID 1295119 반응식
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH:30]([CH2:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:23]2.O[CH2:39][CH2:40][CH2:41][NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[N:44]1[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=1[NH:42][CH2:41][CH2:40][CH2:39][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([CH2:29][CH:30]([CH2:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:23]2

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 114124793-((Pyridin-2-yl)amino)propan-1-olHCID 22570392Methyl 2-[(5-hydroxyindolyl)methyl]pentanoate

생성물 1

HCID 22570346Methyl 2-({5-[3-(2-pyridylamino)propoxy]indolyl}methyl)pentanoate수율 36%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1,1′-(Azodicarbonyl)dipiperidine (0.12 g, 0.48 mmol) was added to the solution of methyl 2-[(5-hydroxyindolyl)methyl]pentanoate (0.03 g, 0.12 mmol), as prepared in the preceding step, 2-(3-hydroxypropyl)aminopyridine (0.026 g, 0.17 mmol), as prepared in step b of Example 1, and tri-n-butylphosphine (0.09 g, 0.46 mmol) in tetrahydrofuran (6.0 mL). After stirring at ambient temperature overnight (16 h), the reaction was concentrated and the residue was purified by flash chromatography on silica gel (10%–50% ethyl acetate in hexane) to give the title compound as a yellow oil (0.016 g, 36%). 1H-NMR (400 MHz, CDCl3) δ 8.08 (m, 1H), 7.39 (m, 1H), 7.20 (d, J=8.9 Hz, 1H), 7.07 (d, J=2.4 Hz, 1H), 7.02 (d, J=3.3 Hz, 1H), 6.88 (dd, J=8.9, 2.4 Hz, 1H), 6.53 (m, 1H), 6.40 (m, 2H), 4.32 (br s, 1H), 4.42 (m, 1H), 4.25 (m, 3H), 3.52 (m, 5H), 2.91 (m, 1H), 2.20 (m, 2H), 1.72 (m, 2H), 1.43 (m, 3H), 0.95 (t, J=7.2 Hz, 3H).

후처리

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (10%–50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-d10d9180ee8d415ca37cb04dd961a752
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241789B2

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