Tetrabutylammonium Fluoride → HCID 9997135, compound

HRID 1245466Notes

Reaction equation

HRID 1245466 reaction equation
CCCC[N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])(CCCC)CCCC.[F-].O1C2C=CC=CC=2C=C1[C:28]1[C:29](=[O:64])[NH:30][C:31](=[O:63])[C:32]=1[C:33]1[C:41]2[C:36](=[N:37][CH:38]=[CH:39][CH:40]=2)[N:35]([CH2:42][CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=1>C1COCC1>[OH:45][CH2:44][CH2:43][CH2:42][N:35]1[C:36]2=[N:37][CH:38]=[CH:39][CH:40]=[C:41]2[C:33]([C:32]2[C:31](=[O:63])[NH:30][C:29](=[O:64])[C:28]=2[C:16]2[CH:15]=[CH:14][NH:5][CH:17]=2)=[CH:34]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21912002HCID 21912002, compound

Product 1

HCID 9997135HCID 9997135, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.12 mL, 1 M solution in THF, 0.12 mmol) as added dropwise to a solution of 3-benzofuran-2-yl-4-{1-[3-(tert-butyldiphenylsilanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrrole-2,5-dione Compound 16a (0.044 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 24 (0.017 g, 84%) as an orange solid. 1H NMR (300 MHz, Acetone-d6) δ 10.47 (s, 1H), 9.57 (s, 1H), 8.3 (dd, J=4.7, 1.5 Hz, 1H), 7.9 (s, 1H), 7.56 (m, 1H), 7.49 (dd, J=7.9, 1.5 Hz, 1H), 7.01 (dd, J=7.9, 4.7 Hz, 1H), 6.75 (m, 1H), 6.22 (m, 1H), 4.55 (t, J=6.6 Hz, 2H), 4.02 (t, J=5.7 Hz, 1H), 3.56 (q, J=5.8 Hz, 2H), 2.11 (m, 2H); MS (ES) m/z: 388 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-fcd2c7ebec224ad9ba45424f3db01cbe
Source dataset
uspto-grants-2006_10
Patent number
US07125878B2

Reaction notes

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