Hydrochloric Acid → (5-Bromopyridin-2-yl)methanamine

HRID 1399912Notes

Reaction equation

HRID 1399912 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.B.C1COCC1.Cl.C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 8171545-Bromopyridine-2-carbonitrileHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 49761678(5-Bromopyridin-2-yl)methanamineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-bromopicolinonitrile (3.0 g, 16.4 mmol) in BH3.THF (99 mL, 99 mmol, 1M) was heated at reflux temperature for 2 h under N2. MeOH (12 mL) was added slowly followed by 1N HCl (24 mL). The mixture was then refluxed for an additional 7 h. After cooling, the reaction mixture was poured into 10% of K2CO3 (300 mL) and extracted with DCM (3×100 ml). The combined organic layers were concentrated to give crude product which was used in next step without further purification (2.1 g, Yield 70%).

Workup

  1. temperatureat reflux temperature for 2 h under N2
  2. temperatureThe mixture was then refluxed for an additional 7 h
  3. temperatureAfter cooling
  4. extractionextracted with DCM (3×100 ml)
  5. concentrationThe combined organic layers were concentrated
  6. customto give crude product which
  7. customwas used in next step without further purification (2.1 g, Yield 70%)

Sources & evidence

ORD record
ord-7bff78f176ea46059f298b6c8844e7c9
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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