m-Toluidine → 3-(2-Bromo-pyridin-4-yloxy)-N-m-tolyl-benzamide

HRID 1402476Notes

Reaction equation

HRID 1402476 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[CH:44]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:42][C:43]2[CH:44]=[C:45]([CH3:49])[CH:46]=[CH:47][CH:48]=2)=[O:14])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 7934m-ToluidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581679363-(2-Bromo-pyridin-4-yloxy)-benzoic acid

Product 1

HCID 581679193-(2-Bromo-pyridin-4-yloxy)-N-m-tolyl-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-bromo-pyridin-4-yloxy)-benzoic acid (170 mg, 0.58 mmol), HATU (265 mg, 0.69 mmol),) m-toluidine (93 mg, 0.87 mmol) and N,N-diisopropylethylamine (164 mg, 1.28 mmol) in anhydrous DMF (10 ml) was stirred at room temperature for 20 minutes. The mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give 3-(2-Bromo-pyridin-4-yloxy)-N-m-tolyl-benzamide as off-white solid. Yield: 150 mg, 68%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d5cc7d62c5264a2aa0fcd9b98b43fa2a
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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