Triethylamine → 4-Methylsulfanyl-[2,2']bipyridinyl-6-carbonitrile

HRID 562872Notes

Reaction equation

HRID 562872 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N+:6]([O-])=[CH:7][CH:8]=1.P([C:24]#[N:25])(=O)(OCC)OCC.C(N(CC)CC)C>C(#N)C>[CH3:1][S:2][C:3]1[CH:8]=[C:7]([C:24]#[N:25])[N:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 592012924-Methylsulfanyl-[2,2']bipyridinyl 1-oxide

Product 1

HCID 569633764-Methylsulfanyl-[2,2']bipyridinyl-6-carbonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methylsulfanyl-[2,2′]bipyridinyl 1-oxide (480 mg, 2.20 mmol) was treated under nitrogen with diethyl phosphorocyanidate and triethylamine in dry acetonitrile following a described procedure (I. Antonioni; G. Cristalli; P. Franchetti; M. Grifantini; S. Martelli, Il Farmaco, 1986, 41, 346-354). Crystallization in ethyl acetate afforded 4-methylsulfanyl-[2,2′]bipyridinyl-6-carbonitrile as a white solid (360 mg, 72% yield)

Workup

  1. customCrystallization in ethyl acetate

Sources & evidence

ORD record
ord-fbfb6f82d4c141a4855306a2a2c7e8ca
Source dataset
uspto-grants-2011_11
Patent number
US08067441B2

Reaction notes

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