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

HRID 925294Notes

Reaction equation

HRID 925294 reaction equation
[C:1](P(=O)(OCC)OCC)#[N:2].[CH3:11][S:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N+:16]([O-])=[CH:17][CH:18]=1.C(N(CC)CC)C>C(#N)C>[CH3:11][S:12][C:13]1[CH:18]=[C:17]([C:1]#[N:2])[N:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 59201292HCID 59201292, compound

Product 1

HCID 569633764-Methylsulfanyl-[2,2']bipyridinyl-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Diethyl cyanophosphonate 90% (1.3 mL, 8.4 mmol) was slowly added at 25° C. to a mixture of 4-Methylsulfanyl-[2,2′]bipyridinyl 1-oxide (650.0 mg, 2.98 mmol) and triethylamine (0.50 mL, 3.58 mmol) in acetonitrile (14 mL) and stirred for 2 hours at 90° C. The reaction mixture was concentrated under reduced pressure, methanol (5 mL) added and the solid formed filtered and washed with methanol (2×5 mL), the filtrate was concentrated and purified by column chromatography on silica gel (0 to 10% Methanol in dichloromethane) to afford 4-methylsulfanyl-[2,2′]bipyridinyl-6-carbonitrile as a white solid that was combined with the previous white solid obtained (500.0 mg, 74%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, methanol (5 mL)
  2. additionadded
  3. customthe solid formed
  4. filtrationfiltered
  5. washwashed with methanol (2×5 mL)
  6. concentrationthe filtrate was concentrated
  7. custompurified by column chromatography on silica gel (0 to 10% Methanol in dichloromethane)

Sources & evidence

ORD record
ord-381c0377108d4ae7aafe393b01e8857e
Source dataset
uspto-grants-2016_03
Patent number
US09284296B2

Reaction notes

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