Chloroacetone → 1-[[4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]oxy]-2-propanone

HRID 914792Notes

Reaction equation

HRID 914792 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:25])[C:19](C(O)(C)C)=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:26])[NH:6]2.Cl[CH2:28][C:29](=[O:31])[CH3:30].C([O-])([O-])=[O:33].[K+].[K+]>CC(C)=O>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:25])[C:19]([O:33][CH2:28][C:29](=[O:31])[CH3:30])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:26])[NH:6]2

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 223379962-{4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl}propan-2-ol

Product 1

HCID 159831941-[[4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]oxy]-2-propanoneYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Example 1 (3.1 g, 10 mmol), chloroacetone (1.02 g, 11 mmol), and K2CO3 (4.1 g, 30 mmol) in acetone (100 mL) was heated at 50° C. for 6 h. The mixture was cooled and concentrated to give a beige solid which was washed with ethyl acetate/dichloromethane (1:1). The filtrate was purified by passing through a short pad of silica gel to afford the desired product (3.34 g, 91% yield) as a light beige solid. MS: (M+H)+=369.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customto give a beige solid which
  4. washwas washed with ethyl acetate/dichloromethane (1:1)
  5. customThe filtrate was purified

Sources & evidence

ORD record
ord-8f7fb6ea24894bedaff4f92298a36b2c
Source dataset
uspto-grants-2007_09
Patent number
US07265113B2

Reaction notes

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