Tetrabutylammonium Fluoride → HCID 10479077, compound

HRID 507258Notes

Reaction equation

HRID 507258 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-379854980dc749c5bc0b13b62cbf7bca
Source dataset
uspto-grants-2010_08
Patent number
US07786135B2

Reaction notes

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