(Dimethyl sulfide)trihydroboron → HCID 13649440, compound

HRID 280205Notes

Reaction equation

HRID 280205 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[N:9]=2)=[CH:4][CH:3]=1.B.CSC>O1CCCC1>[NH2:15][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[N:9]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 13649439HCID 13649439, compound

Product 1

HCID 13649440HCID 13649440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing solution of 1.6 g of 2-(p-bromophenyl)-6-cyano pyridine in 8 ml of tetrahydrofuran is added slowly a solution of 0.92 ml of borane-dimethylsulfide in 6 ml. of tetrahydrofuran. Dimethyl sulfide is simultaneously removed by distillation through a 10 cm vigreux column. The mixture is refluxed for 15 minutes after the addition is complete, cooled to 30°, and 6 ml of 6N hydrochloric acid is added. After hydrogen evolution has ceased, the reaction is refluxed for 30 minutes, cooled to 0°, saturated with solid sodium carbonate and extracted with 4×50 ml aliquots of methylene chloride. The methylene chloride solution is evaporated and the residue is chromatographed through 10.0 g of silica gel with 1:1 methanol-ethyl acetate as eluent to yield 2-aminomethyl-6-(p-bromophenyl)pyridine melting at 71°-75°.

Workup

  1. customDimethyl sulfide is simultaneously removed by distillation through a 10 cm vigreux column
  2. temperatureThe mixture is refluxed for 15 minutes
  3. additionafter the addition
  4. temperaturecooled to 30°
  5. addition6 ml of 6N hydrochloric acid is added
  6. temperaturethe reaction is refluxed for 30 minutes
  7. temperaturecooled to 0°, saturated with solid sodium carbonate
  8. extractionextracted with 4×50 ml aliquots of methylene chloride
  9. customThe methylene chloride solution is evaporated
  10. customthe residue is chromatographed through 10.0 g of silica gel with 1:1 methanol-ethyl acetate as eluent

Sources & evidence

ORD record
ord-ae3133091d0d4c32b8f35f379b7f9eb2
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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