Pyridine → 3-[3-(2-Hydroxy-3,3,3-trichloropropyl)pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 466032Notes

Reaction equation

HRID 466032 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12.[Cl:23][C:24]([Cl:29])([Cl:28])[CH:25](O)[OH:26].N1C=CC=CC=1.C(Cl)Cl>O>[OH:26][CH:25]([C:24]([Cl:29])([Cl:28])[Cl:23])[CH2:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12

Participants

6

Reactant 4

HCID 1049PyridineHCID 2707Chloral HydrateHCID 6344DichloromethaneHCID 151581083-(3-Methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581513-[3-(2-Hydroxy-3,3,3-trichloropropyl)pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 42.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3-methylpyridazin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.40 g), chloral hydrate (0.70 g) and pyridine (4 ml) was stirred for 20 hours at 90°-100° C. After cooling, to the reaction mixture was added methylene chloride (4 ml) and water (4 ml) at room temperature, and stirred for 3 hours. The precipitates were collected by filtration to give 3-[3-(2-hydroxy-3,3,3-trichoropropyl)pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.26 g).

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. stirringstirred for 3 hours
  3. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-174271fbf0524d589fccce4279f7812b
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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