Propylene Oxide → HCID 178468210, compound

HRID 1768569Notes

Reaction equation

HRID 1768569 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:17]1[O:20][CH:18]1[CH3:19]>C1(C)C=CC=CC=1>[OH:20][CH:18]([CH3:19])[CH2:17][N:14]1[CH2:15][CH2:16][CH:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][N:7]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 178505426HCID 178505426, compound

Product 1

HCID 178468210HCID 178468210, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1H-indazole (500 mg, 2.3 mmol) and propylene oxide (1g, 17 mmol) in 25 ml toluene was heated to 50° C. in an autoclave for 7 days. The cooled reaction was concentrated in vacuo and purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (4:1, v/v). Concentration of the appropriate fractions afforded 350 mg (54.9%) of 3-[1-(2-hydroxyprop-1-yl)-4-piperidinyl]-6-fluoro-1 H-indazole as a foam.

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. custompurified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (4:1

Sources & evidence

ORD record
ord-34b3204324c14b0098460db08eaf5860
Source dataset
uspto-grants-1995_01
Patent number
US05378714

Reaction notes

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