Tetrabutylammonium Fluoride → HCID 89662746, compound

HRID 1479098Notes

Reaction equation

HRID 1479098 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][CH2:25][CH:26]([CH3:51])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([N:36]1[CH2:50][C:39]2=[C:40]3[N:45]([N:46]=[C:38]2[CH2:37]1)[C:44]([CH3:47])=[C:43]([Cl:48])[C:42]([CH3:49])=[N:41]3)=[O:35])(C)(C)C>C1COCC1>[Cl:48][C:43]1[C:42]([CH3:49])=[N:41][C:40]2[N:45]([N:46]=[C:38]3[CH2:37][N:36]([C:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][CH:26]([CH3:51])[CH2:25][OH:24])=[O:35])[CH2:50][C:39]3=2)[C:44]=1[CH3:47]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131736559HCID 131736559, compound

Product 1

HCID 89662746HCID 89662746, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of tetrabutyl-ammonium fluoride in THF (1.26 mL; 1.26 mmol; 1.2 eq.) was added to a cold (0° C.) solution of {2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethoxy]-phenyl}-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-methanone (540 mg; 1.05 mmol; 1 eq.) in THF (5 mL) and the resulting mixture was stirred at room temperature for 2.5 hours. After dilution with EA, the solution was washed with sat. aq. NaHCO3, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (50% EA in cyclohexane to EA) afforded the title compound (200 mg, 48%) as a white foam. 1H NMR (DMSO-d6) δ 7.52-7.36 (m, 1H), 7.37-7.23 (m, 1H), 7.23-7.14 (d, J=8.4 Hz, 1H), 7.09-6.96 (m, 1H), 4.96-4.73 (m, 3H), 4.55-4.38 (m, 2H), 3.51-3.37 (m, 2H), 2.84 (s, 1.5H), 2.80 (s, 1.5H), 2.62 (s, 1.5H), 2.55 (s, 1.5H), 1.24-1.11 (dd, J=6.2, 2.3 Hz, 2H). HPLC (max plot) 99.1%, Rt 3.35 min. UPLC/MS: (MS+) 401.2 ([M+H]+).

Workup

  1. washAfter dilution with EA, the solution was washed with sat. aq. NaHCO3
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (50% EA in cyclohexane to EA)

Sources & evidence

ORD record
ord-cfed25e3297e48cdb5835035580b53dd
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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