Cesium carbonate → N-(4-(3-bromopyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine

HRID 410197

Reaction equation

HRID 410197 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[Br:19][C:20]1[C:21](Cl)=[N:22][CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.[Cl-].[Na+].O>[Br:19][C:20]1[C:21]([O:18][C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:3]3[N:2]([CH3:1])[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[N:4]=3)=[CH:13][CH:14]=2)=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 6933243-Bromo-2-chloropyridineHCID 593270144-(1-methyl-1H-benzoimidazol-2-ylamino)-phenol

Product 1

HCID 59327116N-(4-(3-bromopyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a round bottomed flask was added 4-(1-methyl-1H-benzo[d]imidazol-2-ylamino)phenol (1.0058 g, 4.20 mmol), 3-bromo-2-chloropyridine (1.213 g, 6.31 mmol), and cesium carbonate (2.74 g, 8.41 mmol) in DMSO (14.01 mL) at 100° C. to stir. Upon completion, reaction was allowed to cool to room temperature. The reaction mixture was diluted with water (10 mL)/Brine (10 mL) and extracted with DCM (3×15 mL). A precipitate formed during extraction. The solid was filtered to provide N-(4-(3-bromopyridin-2-yloxy)phenyl)-1-methyl-1H-benzo[d]imidazol-2-amine.

Workup

  1. customUpon completion, reaction
  2. extractionextracted with DCM (3×15 mL)
  3. customA precipitate formed during extraction
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-ae882382efb44cd7820fb9523d4e79c5
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Linked notes

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