Methanol → HCID 66711736, compound

HRID 1262326Notes

Reaction equation

HRID 1262326 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:21]2[C:16]([CH:17]=[N:18][C:19]([S:22][CH3:23])=[N:20]2)=[CH:15][CH:14]=1)[S:3]([CH3:6])(=[O:5])=[O:4].CO.[Br:26]N1C(=O)CCC1=O>>[Br:26][C:15]1[CH:14]=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:2]([CH3:1])[S:3]([CH3:6])(=[O:4])=[O:5])[N:21]2[C:16]=1[CH:17]=[N:18][C:19]([S:22][CH3:23])=[N:20]2

Participants

4

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 66711670HCID 66711670, compound

Product 1

HCID 66711736HCID 66711736, compound

Procedure

Into a 1-Neck round-bottom flask, N-Methyl-N-[2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide (0.710 g, 2.04 mmol) Tetrahydrofuran (20.0 mL, 246 mmol), and Methanol (10 mL, 200 mmol) were added under an atmosphere of Nitrogen at room temperature . Recrystallized N-Bromosuccinimide (0.381 g, 2.14 mmol) was added portion wise over 10 minutes. The reaction was stirred at room temperature for 2 hours. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 5% methanol). The collected fractions afforded N-[2-(5-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide a yellow solid (0.72 g, 82%).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 5% methanol)

Sources & evidence

ORD record
ord-06771d02fcd44af9b1bf307014441d19
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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