Potassium Carbonate → HCID 20767704, compound

HRID 1163057Notes

Reaction equation

HRID 1163057 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.Br[CH2:28][CH2:29][CH2:30][OH:31].C(=O)([O-])[O-:33].[K+].[K+]>C(#N)C>[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][CH2:29][CH2:30][OH:31])=[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 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 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 20767704HCID 20767704, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 1 (50 mg, 0.16 mmol), 3-bromo-1-propanol (100 μL, 1.1 mmol) and potassium carbonate (100 mg, 0.72 mmol) in acetonitrile (1.5 mL) was stirred overnight at 35° C. The mixture was filtered, concentrated and purified by chromatography on silica gel eluting with 30% ethyl acetate in dichloromethane to provide the title compound (26 mg, 39% yield) as a light beige solid. MS: (M+H)+=371

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel eluting with 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-25be05be8667496184f6710bb3be944b
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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