Pyridinium chloride → HCID 22221635, compound

HRID 1836057Notes

Reaction equation

HRID 1836057 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.Cl.N1C=CC=CC=1>O>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[C:5]([CH2:20][C:21]([F:24])([F:22])[F:23])=[CH:4][C:3]([OH:2])=[CH:19][C:7]=3[CH:8]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22221626HCID 22221626, compound

Product 1

HCID 22221635HCID 22221635, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 140 (50 mg, 0.15 mmol) and Pyridine HCl (3 g) was heated to 200° C. After 1 hr, the reaction was cooled, diluted with water and extracted with EtOAc. The EtOAc was dried over MgSO4, concentrated to give a solid which was triturated with CH2Cl2 and filtered to give 141 (30 mg, 65%): Mp=210-213° C.; 1H NMR(DMSO-d6) δ 9.86 (s, 1 H), 9.28 (s, 1 H), 7.71 (d, 2 H, J=8.8 Hz), 7.05 (s, 1 H), 6.89-6.86 (m, 3 H), 6.69 (d, 1 H, J=2.0 Hz), 3.91-3.84 (m, 2 H); MS 307 [M−H]−

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe EtOAc was dried over MgSO4
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with CH2Cl2
  7. filtrationfiltered

Sources & evidence

ORD record
ord-752bdf501db1478f85f73b2d57810a46
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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