Tetrabutylammonium Fluoride → HCID 9977487, compound

HRID 645923Notes

Reaction equation

HRID 645923 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[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>[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[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][OH:45])[CH:34]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21912002HCID 21912002, compound

Product 1

HCID 9977487HCID 9977487, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.1 mL, 0.1 mmol; 1 M solution in THF) was 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 17a (0.04 g, 0.064 mmol) in THF (1 mL) under nitrogen. After 18 hours, the mixture was concentrated and purified by column chromatography (SiO2) to give Compound 25 (0.022 g, 89%) as an orange solid. 1H NMR (300 MHz, DMSO-d6) δ 11.31 (s, 1H), 8.32 (dd, J=4.7, 1.5 Hz, 1H), 8.27 (s, 1H), 7.77 (m, 1H), 7.65 (s, 1H), 7.57 (dd, J=7.9, 1.3 Hz, 1H), 7.29 (m, 3H), 7.02 (dd, J=7.9, 4.5 Hz, 1H), 4.47 (t, J=6.9 Hz, 2H), 3.5 (t, J=6.0 Hz, 2H), 2.05 (m, 2H); MS (ES) m/z: 388 (M+H+).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-e99e1366e2e94decbb5a3969e4699ea2
Source dataset
uspto-grants-2010_04
Patent number
US07705015B2

Reaction notes

Loading…