Pyridinium, 1-amino-, iodide (1:1) → HCID 18446592, compound

HRID 1269080Notes

Reaction equation

HRID 1269080 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH:10]([OH:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.[I-].[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([CH:10]([OH:12])[CH3:11])=[N:14][N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 18446620HCID 18446620, compound

Product 1

HCID 18446592HCID 18446592, compoundYield 460%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(2-fluoro-4-pyridinyl)-3-butyn-2-ol (1.4 g, 8.5 mmol), aminopyridinium iodide (2.2 g, 9.8 mmol), 1,8-diazobicyclo[5.4.0]undec-7-ene (1.9 mL, 12.7 mmol), and acetonitrile (20 mL) were allowed to stir for 12–16 hours at room temperature. When judged to be complete, the mixture was partitioned between ethyl acetate and water, the organics were washed with brine, dried over magnesium sulfate, filtered and suspended onto silica gel. The crude material was purified by flash chromatography (1:1 hexanes:ethyl acetate) to provide 1-[3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-2-yl]ethanol (1.0 g, 460%) as a beige solid. 1H NMR (DMSO-d6): δ 8.79 (d, 1H), 8.30 (d, 1H), 7.87 (d, 1H), 7.67 (d, 1H), 7.50 (s, 1H), 7.41 (m, 1H), 7.04 (m, 1H), 5.57 (m, 1H), 5.03 (m, 1H), 1.56 (d, 3H).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washthe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe crude material was purified by flash chromatography (1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-250b2dd7dc654ea39c9956f033fd86ba
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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