4-Bromo-3-fluoro-N-methyl-2-nitroaniline → 4-[2-Fluoro-4-(methylamino)-3-nitrophenyl]-6-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056997Notes

Reaction equation

HRID 1056997 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[F:13].[CH3:14][N:15]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[C:18]2[CH:30]=[CH:31][N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:17]=2[C:16]1=[O:41]>>[F:13][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[C:5]([NH:6][CH3:7])[CH:8]=[CH:9][C:2]=1[C:19]1[C:18]2[CH:30]=[CH:31][N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:40])[CH3:39])[C:17]=2[C:16](=[O:41])[N:15]([CH3:14])[CH:20]=1

Participants

3

Reactant 2

HCID 1180938324-Bromo-3-fluoro-N-methyl-2-nitroanilineHCID 1232108536-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Product 1

HCID 1235864014-[2-Fluoro-4-(methylamino)-3-nitrophenyl]-6-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Procedure

This compound was synthesized according to the procedure of Example 10, Step 5, using 4-bromo-3-fluoro-N-methyl-2-nitroaniline and 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one as the starting materials. LCMS calculated for C21H28FN4O4Si (M+H)+: m/z=447.2. found: 447.1.

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-6cfa683b8471443b9695c343f6c84ba3
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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