Dimethylformamide → 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

HRID 451146Notes

Reaction equation

HRID 451146 reaction equation
CN(C=O)C.[CH3:6][N:7]1[CH:11]=[C:10](B(OCC)OCC)[CH:9]=[N:8]1.Br[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=1[O:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>CO.[Cl-].[NH4+].[Fe]>[CH3:30][O:29][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=1[C:10]1[CH:9]=[N:8][N:7]([CH3:6])[CH:11]=1)[NH2:26]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1012932-Bromo-5-nitroanisoleHCID 66709077Diethyl (1-methyl-1H-pyrazol-4-yl)boronate

Product 1

HCID 584144723-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21190736Ammonium chloride methanolSolvent

Procedure

A DMF solution of diethyl 1-methyl-1H-pyrazol-4-ylboronate, 4-bromo-3-methoxy nitrobenzene together with Pd(dppf) and K2CO3 were heated at reflux overnight. The product obtained was reduced with Fe in MeOH/ammonium chloride to provide the title compound. LC-MS (M+H)+=204.2. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.84 (1H, s), 7.66 (1H, s), 7.19 (1H, J=8.2 Hz, d), 6.29 (1H, s), 6.18 (1H, J=2.0, 8.2 Hz, dd), 5.31 (2H, br s), 3.80 (3H, s), 3.75 (3H, s).

Workup

  1. temperatureat reflux overnight
  2. customThe product obtained

Sources & evidence

ORD record
ord-a0e15c5870e44026bc3438777036805a
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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