Phosphorus trichloride → 7-Chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridine

HRID 468862Notes

Reaction equation

HRID 468862 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([I:20])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N+:8]([O-])=[CH:9]2)=[CH:4][N:3]=1.P(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([I:20])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:8]=[CH:9]2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 866749537-Chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridine 2-oxide

Product 1

HCID 866749547-Chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridineYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridine 2-oxide (870 mg, 2.1 mmol) in dichloromethane (13 mL) was added phosphorus trichloride (0.2 mL, 2.3 mmol). The reaction mixture was stirred at room temperature for 1 hour, and then diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford an orange residue that was purified by flash chromatography (silica, 40 g, ISCO, 0-30% ethyl acetate in heptane) to afford the title compound as an orange solid (400 mg, 50%). 1H NMR (400 MHz, CDCl3) δ 9.40 (s, 1H), 9.21 (s, 1H), 7.83 (s, 1H), 7.57-7.53 (m, 1H), 7.49-7.40 (m, 2H), 7.40-7.35 (m, 1H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford an orange residue that
  7. customwas purified by flash chromatography (silica, 40 g, ISCO, 0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-bb040f7ba71340a29ef15c1d6229512c
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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