Methanesulfonic Acid → N-tetrahydropyranyl-2-hydroxycarbazole

HRID 1424387노트

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HRID 1424387 반응식
CC1C=C(C)N(C2C=C(C=CC=2)OC2C=CC3C4C(=CC=CC=4)NC=3C=2)N=1.CC1C=C(C)N(C2C=C(C=CC=2)[O:38][C:39]2[CH:51]=[CH:50][C:49]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[N:42]([CH:52]4[CH2:57][CH2:56][CH2:55][CH2:54][O:53]4)[C:41]=3[CH:40]=2)N=1.S(O)(C)(=O)=O.C(=O)(O)[O-].[Na+]>CO.CCCCCC.C(OCC)(=O)C>[O:53]1[CH2:54][CH2:55][CH2:56][CH2:57][CH:52]1[N:42]1[C:41]2[CH:40]=[C:39]([OH:38])[CH:51]=[CH:50][C:49]=2[C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2

참가 물질

7

반응물 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 681812542-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazoleHCID 681813132-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole

생성물 1

HCID 68181306N-tetrahydropyranyl-2-hydroxycarbazole수율 81%

시약·촉매·용매 2

HCID 887Methanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

In another step, 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazole was synthesized. To a 50 mL round flask was added with the solution of 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole (0.49 g, 1.12 mmol) and MsOH (0.36 mL, 5.6 mmol) in methanol (20 mL), and the mixture was kept at rt for 30 minutes then 50° C. for 1.5 hours. TLC showed that all the protected starting material was transferred, and then trace sodium bicarbonate was added into the system to quench the reaction. The resulting product was directly treated with an flash column using hexane/ethyl acetate=3:1 as eluent to give N-tetrahydropyranyl-2-hydroxycarbazole as a white solid. (0.32 g, 81% yield).

후처리

  1. wait50° C. for 1.5 hours
  2. additionwas added into the system
  3. customto quench
  4. customthe reaction
  5. additionThe resulting product was directly treated with an flash column

출처 및 근거

ORD 기록
ord-0ea606f5175642c78123caa9f786415b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927713B2

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