Sodium hydride → [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine

HRID 985486Notes

Reaction equation

HRID 985486 reaction equation
[H-].[Na+].[CH:3]([Si:6]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[SH:7])([CH3:5])[CH3:4].[H][H].I[C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1>C1COCC1.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][CH:11]([Si:6]([CH:3]([CH3:5])[CH3:4])([S:7][C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1)[CH:8]([CH3:10])[CH3:9])[CH3:13]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 22507076HCID 22507076, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22507077[6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamineYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (128 mg, 5.1 mmol) in THF (30 ml) was added triisopropylsilanethiol (1.1 ml, 5.1 mmol) dropwise. After the evolution of hydrogen ceased, a solution of {6-[2-(3-Iodophenoxy)ethyl](2-pyridyl) }methylamine (1.2 g, 3.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (390 mg, 0.3 mmol) in toluene (30 ml) was added. After refluxing for 16 h under argon, the reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was dissolved in ethyl acetate and washed with 1N NaOH and brine. The organic layer was dried with sodium sulfate, filtered, and evaporated. The crude product was chomatrographed over silica gel to yield 1.34 g (95%) of [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine. NMR 1H Cl3CD δ: 7.38 (dd, 1H, J=7.2, 8.0 Hz), 7.04 (m, 3H), 6.77 (m, 1H), 6.52 (d, 1H, J=8.0 Hz), 6.25 (d, 1H, J=4.0 Hz), 4.29 (t, 2H, J=6.8 Hz), 3.06 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8Hz), 1.85 (m, 3H), 1.09 (m, 2H).

Workup

  1. temperatureAfter refluxing for 16 h under argon
  2. customevaporated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-67852ab832a540cea70b7882f6b9f223
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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