Tetrabutylammonium Fluoride → HCID 9997135, compound

HRID 507256Notes

Reaction equation

HRID 507256 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-62f206953f1949969b3a91cf3114cb08
Source dataset
uspto-grants-2010_08
Patent number
US07786135B2

Reaction notes

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