Ethyl Acetate → HCID 87214300, compound

HRID 914790Notes

Reaction equation

HRID 914790 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.[C:27]([O-:30])([O-])=O.[K+].[K+].[C:33](OCC)(=[O:35])[CH3:34]>CN(C=O)C>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:25])[C:19]([O:35][CH2:33][C@@H:34]4[CH2:27][O:30]4)=[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 8857Ethyl AcetateHCID 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 87214300HCID 87214300, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 1 (311 mg, 1 mmol), (2S)-(+)-glycidyl nosylate (311 mg, 1.2 mmol), and K2CO3 (200 mg, 1.45 mmol) in DMF (3 mL) was stirred at RT for 4 hr. The mixture was diluted with ethyl acetate and the solids were filtered. The filtrate was washed with brine, dried, and concentrated. The residue was purified by flash column chromatography (silica gel, 50% ethyl acetate in hexanes) to afford the title compound (340 mg, 92% yield). LC/MS; (M+H)+=369.1

Workup

  1. filtrationthe solids were filtered
  2. washThe filtrate was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c8dedf8352aa4c2f91991e45493b68b3
Source dataset
uspto-grants-2007_09
Patent number
US07265113B2

Reaction notes

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