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Methyl iodide → (4-(3-Bromopyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[D]imidazol-2-YL)methanone

HRID 1880022
Notes
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Reaction equation

HRID 1880022 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[C:26](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(Cl)Cl>[Br:25][C:24]1[C:19]([O:18][C:15]2[CH:14]=[CH:13][C:12]([C:10]([C:2]3[N:3]([CH3:26])[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)=[O:11])=[CH:17][CH:16]=2)=[N:20][CH:21]=[CH:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59326957(1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone

Product 1

HCID 59327020(4-(3-Bromopyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[D]imidazol-2-YL)methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)-phenyl)methanone (0.5 g, 1 mmol) in DMF (3 mL) was added cesium carbonate (0.5 g, 2 mmol) and iodomethane (0.2 g, 1 mmol). Reaction was stirred at RT overnight. Reaction mixture was diluted with DCM and washed with water and brine. Purification by prep HPLC produced the desired product.

Workup

  1. customReaction
  2. customReaction mixture
  3. washwashed with water and brine
  4. customPurification by prep HPLC

Sources & evidence

ORD record
ord-72eec0d5f6be4c658668efc4fe21a48c
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318718B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes