N-Iodosuccinimide → 2-(4-Fluorophenyl)-7-iodo-3-pyridin-4-ylpyrazolo[1,5-a]pyridine

HRID 1373833Notes

Reaction equation

HRID 1373833 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[I:28]N1C(=O)CCC1=O>O1CCCC1.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([I:28])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 98571462-(4-Fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridineHCID 178418339Butyllithium

Product 1

HCID 102732702-(4-Fluorophenyl)-7-iodo-3-pyridin-4-ylpyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2-(4-fluorophenyl)-3-(4-pyridyl)-pyrazolo[1,5-α]pyridine (100 mg, 0.346 mmol) in 4 mL of tetrahydrofuran at −78° C. under N2 was added 2.5 M n-butyllithium in hexanes (2 eq.). The mixture was stirred at −78° C. for 30 min and N-iodosuccinimide (2.2 eq.) was then added. The mixture was allowed to warm to room temperature after 30 min and was stirred at room temperature for 1 hour. The mixture was diluted with ether and washed with 1N hydrochloric acid solution. The aqueous layer was basified with 1 N sodium hydroxide solution and extracted thoroughly with ether. The combined organic layers were dried on anhydrous magnesium sulfate, filtered and evaporated. Purification by chromatography yielded 2-(4-fluorophenyl)-7-iodo-3-pyridin-4-ylpyrazolo[1,5-α]pyridine as a yellow solid. 1H NMR (CDCl3): δ 8.54 (d, 2H, J=5.8 Hz), 7.50–7.57 (m, 3H), 7.37 (d, 1H, J=7.1 Hz), 7.20 (d, 2H, J=5.8 Hz), 7.00 (t, 2H, J=8.6 Hz), 6.90 (t, 1H, J=7.8 Hz); MS m/z 416 (M+1).

Workup

  1. temperatureto warm to room temperature after 30 min
  2. stirringwas stirred at room temperature for 1 hour
  3. washwashed with 1N hydrochloric acid solution
  4. extractionextracted thoroughly with ether
  5. dry with materialThe combined organic layers were dried on anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography

Sources & evidence

ORD record
ord-0861cc3cf2cb4bc2b48884e15e4d4d55
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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