Benzyltriphenylphosphonium bromide → N-(3-(2-Phenylvinyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392438

Reaction equation

[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:38]([C:40]1[CH:41]=[C:42]([N:46]([CH2:52][C:53]2[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=2)[S:47]([CH2:50][CH3:51])(=[O:49])=[O:48])[CH:43]=[CH:44][CH:45]=1)=O>C1COCC1>[C:3]1([CH:2]=[CH:38][C:40]2[CH:41]=[C:42]([N:46]([CH2:52][C:53]3[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=3)[S:47]([CH2:50][CH3:51])(=[O:49])=[O:48])[CH:43]=[CH:44][CH:45]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyltriphenylphosphonium bromide (0.765 g, 1.77 mmol) was dispersed into THF (12 ml) and cooled at 0° C. To the cooled suspension was added dropwise a solution of potassium bis(trimethylsilyl)amide (0.5 M, 3.5 ml, 1.75 mmol). After stirring at 0° C. for 1 h, a solution of). N-(3-formyl-phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.304 g, 1.0 mmol) in THF was added. The reaction mixture was stirred at ambient temperature for 2 h. Evaporation and chromatography on silica-gel eluting with toluene-EtOAc to give the title compound. 1H NMR: 8.48 (d,1H,J=3.4 Hz), 8.30 (d,1H,J=2.0 Hz), 7.65 (d,1H,J=7.8 Hz), 7.30-6.74 (m,8H), 6.60 (q,2H,J=12.2, 37.1 Hz), 4.68 (s,2H), 2.87 (q,2H,J=7.3 Hz), 1.28 (t,3H,J=7.4 Hz). MS calcd 378.1; MS (M+1) 379.1.

Workup

stirringThe reaction mixture was stirred at ambient temperature for 2 h
customEvaporation and chromatography on silica-gel
washeluting with toluene-EtOAc

Sources & evidence

ORD record: ord-5f86ebaf8dca4cb699ef961509a0e398
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Linked notes

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