Tetrabutylammonium Fluoride → Ethyl 5-(3-{2-[6-(Methylamino)(2-pyridyl)]ethoxy}phenylthio)4-oxopentanoate

HRID 985487Notes

Reaction equation

HRID 985487 reaction equation
CC([Si](C(C)C)([S:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][CH2:13][CH2:14][C:15]1[N:20]=[C:19](CN)[CH:18]=[CH:17][CH:16]=1)C(C)C)C.[F-].[CH2:30]([N+:34](CCCC)(CCCC)CCCC)CCC.Br[CH2:48][C:49](=[O:57])[CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53]>C1COCC1>[CH3:30][NH:34][C:19]1[N:20]=[C:15]([CH2:14][CH2:13][O:12][C:11]2[CH:10]=[C:9]([S:8][CH2:48][C:49](=[O:57])[CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH:25]=[CH:24][CH:23]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 12397184Ethyl 5-bromo-4-oxopentanoateHCID 22507077[6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine

Product 1

HCID 22507074Ethyl 5-(3-{2-[6-(Methylamino)(2-pyridyl)]ethoxy}phenylthio)4-oxopentanoateYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [6-(2-{3-[1,1-bis(Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine (1.34 g, 3.2 mmol) and THF (25 ml) under Argon, was added tetrabutylamonium floride (3.5 ml, 3.5 mmol, 1M in THF) at room temperature. After stirring for 15 minutes, a solution of ethyl 5-bromo-4-oxopentanoate (0.79 g, 3.5 mmol) in THF (5 ml) was added. The mixture was stirred for 3 h. The solvent was removed under vacuum and the remaining residue was chromatographed over silica gel to yield 830 mg (64%) of Ethyl 5-(3-{2-[6-(Methylamino)(2-pyridyl)]ethoxy }phenylthio)-4-oxopentanoate. NMR 1H Cl3CD δ: 7.38 (dd, 1H, J=7.2, 8.0 Hz), 7.17 (t, 1H, J=8.0 Hz), 6.89 (m, 2H), 6.71 (m, 1H), 6.54 (d, 1H, J=8.0 Hz), 6.25 (d, 1H, J=4.0 Hz), 4.30 (t, 2H, J=6.8 Hz), 4.13 (c, 2H, J=7.2 Hz), 3.72 (s, 2H), 3.07 (t, 2H, J=6.8 Hz), 2.91(m, 5H), 2.59 (t, 2H, J=6.8 Hz), 1.24 (t, 3H, J=7.2 Hz).

Workup

  1. stirringThe mixture was stirred for 3 h
  2. customThe solvent was removed under vacuum
  3. customthe remaining residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-bc5299296fb542d293a6a43a7493b8b1
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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