Tetrabutylammonium Fluoride → HCID 59596305, compound

HRID 2264724Notes

Reaction equation

HRID 2264724 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Br:37])[CH:32]=2)([C:17]2[CH:22]=[CH:21][C:20]([O:23][Si](C(C)(C)C)(C)C)=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Br:37])[CH:32]=2)([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59596277HCID 59596277, compound

Product 1

HCID 59596305HCID 59596305, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To {3-(3-bromo-phenyl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3H-isoindol-1-yl}-carbamic acid tert-butyl ester (Scheme #6, R) (1.07 g, 1.80 mmol) in tetrahydrofuran (20 mL) was added 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (1.98 mL, 1.98 mmol). After 10 minutes the reaction was quenched with water (50 mL) and extracted twice with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride, dried over magnesium sulfate and the solvent removed under reduced pressure to give a yellow oil. This was chromatographed on 20 g silica gel eluting with 40% ethyl acetate/hexanes and the combined purified fractions removed of solvent under reduced pressure to give the title compound as a yellow solid (906 mg, quantitative yield). 1H NMR (300 MHz, DMSO-d6/TFA-d) δ 8.64 (d, J=7.7 Hz, 1 H), 7.89 (t, J=7.7 Hz, 1 H), 7.74 (t, J=7.5 Hz, 2 H), 7.61-7.57 (m, 2 H), 7.33 (dd, J=4.7, 1.2 Hz, 2 H), 7.14 (dd, J=6.8, 1.9 Hz, 2 H), 6.78 (d, J=8.9 Hz, 2 H), 1.62 (s, 9 H); MS (APCI+) m/z 479 [M+1]+; tR=2.23 min.

Workup

  1. customAfter 10 minutes the reaction was quenched with water (50 mL)
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customto give a yellow oil
  7. customThis was chromatographed on 20 g silica gel eluting with 40% ethyl acetate/hexanes
  8. customthe combined purified fractions
  9. customremoved of solvent under reduced pressure

Sources & evidence

ORD record
ord-f2c986f3738643d9916ae34f53c35da5
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

Loading…