Cyclopentanone → 6-Bromo-N-cyclopentylpyridin-3-amine

HRID 646158Notes

Reaction equation

HRID 646158 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[C:9]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10]1.[BH3-]C#N.[Na+]>C(Cl)Cl.C(OC)(C)(C)C.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8452CyclopentanoneHCID 6428116-Bromopyridin-3-amineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 722192236-Bromo-N-cyclopentylpyridin-3-amineYield 40%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 6-bromopyrid-3-ylamine (2.0 g, 11.6 mmol) in CH2Cl2 (30 mL) was added cyclopentanone (1.3 mL) 15.5 mmol), followed by TiCl4 (1.4 mL, 12.7 mmol) in CH2Cl2 (20 mL) and after stirring for 3.5 h at room temperature, NaBH3CN (2.17 g, 34.5 mmol) was added portion-wise. The reaction was left to stir overnight at ambient temperature, diluted with t-BuOMe (200 mL), washed with water, brine and dried (Na2SO4). Solvent removal and purification by chromatography afforded the sub-title compound (880 mg, 40%).

Workup

  1. waitThe reaction was left
  2. stirringto stir overnight at ambient temperature
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent removal and purification by chromatography

Sources & evidence

ORD record
ord-f0b24163ef3848d79482bc5fac0d4c0f
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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