Methanesulfonic Acid → N-tetrahydropyranyl-2-hydroxycarbazole

HRID 1424387Notes

Reaction equation

HRID 1424387 reaction equation
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

Participants

7

Reactant 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

Product 1

HCID 68181306N-tetrahydropyranyl-2-hydroxycarbazoleYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0ea606f5175642c78123caa9f786415b
Source dataset
uspto-grants-2015_01
Patent number
US08927713B2

Reaction notes

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