2-(Methanesulfonylamino)phenylboronic acid pinacol ester → N-[2-(6-Methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

HRID 1262072Notes

Reaction equation

HRID 1262072 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])O1.Br[C:22]1[N:30]2[C:25]([CH:26]=[N:27][C:28]([S:31][CH3:32])=[N:29]2)=[CH:24][C:23]=1[CH3:33]>>[CH3:33][C:23]1[CH:24]=[C:25]2[N:30]([C:22]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[N:29]=[C:28]([S:31][CH3:32])[N:27]=[CH:26]2

Participants

3

Reactant 2

HCID 43565252-(Methanesulfonylamino)phenylboronic acid pinacol esterHCID 667115157-Bromo-6-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66710834N-[2-(6-Methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

Procedure

N-[2-(6-Methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide was prepared in an analogous fashion to Example 47a after: replacing 2-methoxybenzeneboronic acid with N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide, and replacing 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine with 7-Bromo-6-methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine, to give after purification via normal phase chromatography (EtOAc/hexane as eluant) N-[2-(6-Methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide as a yellow solid (0.12 g, 44%). LC/MS (E/I+) 349.04 (M+H).

Workup

  1. customto give
  2. customafter purification via normal phase chromatography (EtOAc/hexane as eluant) N-[2-(6-Methyl-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide as a yellow solid (0.12 g, 44%)

Sources & evidence

ORD record
ord-2413f8b4f8114095ba612c27772b753f
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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