1,2-Dibromoethane → HCID 22508881, compound

HRID 914788Notes

Reaction equation

HRID 914788 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:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-:32].[K+].[K+]>C(#N)C.ClCCl>[Br:27][CH2:28][CH2:29][O:32][C:19]1[C:18]([CH3:25])=[C:17]2[N:16]([CH:20]=1)[N:15]=[CH:14][N:13]=[C:12]2[O:11][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([CH3:26])=[CH:4]2

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 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 22508881HCID 22508881, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 1 (300 mg, 0.96 mmol), 1,2-dibromoethane (1.5 mL, 17.4 mmol), and potassium carbonate (1.0 g, 7.2 mmol) in acetonitrile (10 mL) was heated at 50° C. for 6 h. The mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica gel eluting with 10% ethyl acetate in dichloromethane to provide the title compound (405 mg, 100%) as a white solid. MS: (M+H)+=419.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified by chromatography on silica gel eluting with 10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-901b82f5ffba498fb288674147f69963
Source dataset
uspto-grants-2007_09
Patent number
US07265113B2

Reaction notes

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