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

HRID 1056956Notes

Reaction equation

HRID 1056956 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[F:20].[CH3:21][N:22]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[C:25]2[CH:37]=[CH:38][N:39]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:24]=2[C:23]1=[O:48]>>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:26]2[C:25]3[CH:37]=[CH:38][N:39]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:47])[CH3:46])[C:24]=3[C:23](=[O:48])[N:22]([CH3:21])[CH:27]=2)=[C:3]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[C:4]=1[N+:9]([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 1180939204-Bromo-3-(2,4-difluorophenoxy)-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 1232420824-[4-Amino-2-(2,4-difluorophenoxy)-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-(2,4-difluorophenoxy)-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 C26H29F2N4O5Si (M+H)+: m/z=543.2. found: 543.2.

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-017cfd004877476d8c38f8803db4752c
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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