2-Fluorophenylboronic acid → 8-(2-Fluoro-phenyl)-quinoxaline-5-carboxylic acid [4-(2-dimethylamino-ethoxy)phenyl]-amide

HRID 2391789Notes

Reaction equation

HRID 2391789 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[C:30]2[N:29]=[CH:28][CH:27]=[N:26][C:25]=2[C:24]([C:31](O)=[O:32])=[CH:23][CH:22]=1.FC1C=CC=CC=1B(O)O>C(Cl)Cl.CO>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:31]([C:24]2[C:25]3[N:26]=[CH:27][CH:28]=[N:29][C:30]=3[C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[F:14])=[CH:22][CH:23]=2)=[O:32])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 27343542-Fluorophenylboronic acidHCID 64846554-[2-(Dimethylamino)ethoxy]anilineHCID 66914618HCID 66914618, compound

Product 1

HCID 445153538-(2-Fluoro-phenyl)-quinoxaline-5-carboxylic acid [4-(2-dimethylamino-ethoxy)phenyl]-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but stirring the reaction mixture overnight and using 4-(2-dimethylamino-ethoxy)-phenylamine (Step 5.1) and 8-(2-fluoro-phenyl)-quinoxaline-5-carboxylic acid. The latter compound was prepared as described in Steps 1.2-1.7 but using 2-fluorophenylboronic acid in Step 1.4. Title compound: ESI-MS: 431.0 [M+H]+; tR=3.93 min (System 1); TLC: Rf=0.29 (DCM/MeOH/NH3aq, 96:3:1).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customThe latter compound was prepared

Sources & evidence

ORD record
ord-6472635819f5491bb0536ecb328652aa
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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