Tetrabutylammonium Fluoride → HCID 10479077, compound

HRID 505375Notes

Reaction equation

HRID 505375 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-78153f6c76bf486898fc67d290561ac4
Source dataset
uspto-grants-2010_08
Patent number
US07781450B2

Reaction notes

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