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

HRID 80234

Reaction equation

HRID 80234 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH:12]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCCCCC.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH2:12][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 98.2%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.1 mL) was added to a stirred solution of 3-bromo-pyridine-4-carbaldehyde (220 mg, 1.18 mmol) and pyrrolidine (0.11 mL, 1.34 mmol) in DCE (15 mL) under nitrogen atmosphere and stirred at room temperature for 2 hours. This was followed by addition of NaBH(OAc)3 (342 mg, 1.612 mmol) at 0° C. over a period of 10 minutes. The resulting reaction mass was stirred for 12 hours at room temperature. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was washed with NaHCO3 solution and extracted using ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to afford 275 mg of the product (98.2% yield).

Workup

  1. customThe resulting reaction mass
  2. stirringwas stirred for 12 hours at room temperature
  3. washThe reaction mixture was washed with NaHCO3 solution
  4. extractionextracted
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6931c758e9b64d3abd05092f2e3a5a5a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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