Acetic Acid → 3-Bromo-4-(pyrrolidin-1-ylmethyl)pyridine

HRID 1843968Notes

Reaction equation

HRID 1843968 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCCCCC.C(OC(=O)C)C>[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH2:8][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 596361363-Bromo-4-(pyrrolidin-1-ylmethyl)pyridineYield 96.52%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Catalytic amount of acetic acid (0.3 mL) was added to a mixture of 3-bromoisonicotinaldehyde (200 mg, 1.075 mmol) and pyrrolidine (0.12 mL, 1.34 mmol) in DCE (20 mL) under nitrogen atmosphere and the resulting mixture was stirred at room temperature for 2.3 hours. This was followed by the addition of sodium triacetoxy-borohydride (342 mg, 1.612 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was washed with NaHCO3 solution and separated the layers. The organic layer was dried over Na2SO4 and concentrated to afford 250 mg of the product (96.52% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washThe reaction mixture was washed with NaHCO3 solution
  3. customseparated the layers
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e993270ffbbd4f8f8c0f75807bf2bc26
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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