Tetrabutylammonium Fluoride → HCID 10479077, compound

HRID 2112808Notes

Reaction equation

HRID 2112808 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:36][CH2:37][CH2:38][CH2:39][N:40]1[C:44]2=[N:45][CH:46]=[CH:47][CH:48]=[C:43]2[C:42]([C:49]2[C:50](=[O:68])[NH:51][C:52](=[O:67])[C:53]=2[C:54]2[C:59]3[S:60][C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=4[C:58]=3[CH:57]=[CH:56][CH:55]=2)=[CH:41]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH:57]1[C:58]2[C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][C:61]=3[S:60][C:59]=2[C:54]([C:53]2[C:52](=[O:67])[NH:51][C:50](=[O:68])[C:49]=2[C:42]2[C:43]3[C:44](=[N:45][CH:46]=[CH:47][CH:48]=3)[N:40]([CH2:39][CH2:38][CH2:37][OH:36])[CH:41]=2)=[CH:55][CH:56]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21911992HCID 21911992, compound

Product 1

HCID 10479077HCID 10479077, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.85 mL, 0.085 mmol; 1 M solution in THF) was added dropwise to a solution of 3-{1-[3-(tert-butyldiphenylsilanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-dibenzothiophen-4-yl-pyrrole-2,5-dione Compound 19a (0.039 g, 0.06 mmol) in THF (1 mL) under nitrogen. After 18 hours the mixture was concentrated and purified by column chromatography (SiO2) to give Compound 28 (0.017 g, 67%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 8.35 (dd, J=7.7, 1.5 Hz 1H), 8.25 (s, 1H), 8.21 (dd, J=6.8.3, 1.5 Hz, 1H), 8.01 (dd, J=4.7, 1.5 Hz, 1H), 7.68 (m, 3H), 7.39 (m, 2H), 6.68 (dd, J=8.1, 1.5 Hz, 1H), 6.55 (dd, J=8.1, 4.7 Hz, 1H), 4.42 (t, J=6.8 Hz, 2H), 3.49 (t, J=6.2 Hz, 2H), 2.03 (m, 2H); MS (ES) m/z: 454 (M+H+).

Workup

  1. concentrationAfter 18 hours the mixture was concentrated
  2. custompurified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-2cffd4556b384233b9ca040d3d35d3e9
Source dataset
uspto-grants-2009_04
Patent number
US07524858B2

Reaction notes

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