Triethylamine → 3-bromo-7-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1742424Notes

Reaction equation

HRID 1742424 reaction equation
[Br:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.O=P(Cl)(Cl)[Cl:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([Cl:14])[CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 115067543-Bromo-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide

Product 1

HCID 678430763-bromo-7-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-6,7-dihydro-5H-[1]pyrindine N-Oxide (250 mg, 1.17 mM) in 3 mL of CH2Cl2 at room temperature was added POCl3 (0.131 mL, 1.4 mM) and triethylamine (0.202 mL, 1.4 mM). The reaction was stirred at room temperature for 2 hours then was extracted from saturated NaHCO3 solution into ethyl acetate, washed with saturated NaCl, dried over MgSO4, filtered, and concentrated to dryness. The product was used crude in the next step. 1H NMR (CDCl3): d 8.60 (s, 1 H), 7.80 (s, 1 H), 5.40 (d, 1 H), 3.00 (m, 2 H), 2.20 (m, 2 H)

Workup

  1. extractionthen was extracted from saturated NaHCO3 solution into ethyl acetate
  2. washwashed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-808d67f9156c4dc2916c1831155253bd
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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