Methanesulfonic Acid → N-tetrahydropyranyl-2-hydroxycarbazole

HRID 2410267ノート

反応式

HRID 2410267 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 68181306N-tetrahydropyranyl-2-hydroxycarbazole収率 81%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b3eb91705b94dd2a3458beca6396da6
出典データセット
uspto-grants-2014_08
特許番号
US08816080B2

反応ノート

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