Potassium Carbonate → (4-(3-ethynylpyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

HRID 410158Notes

Reaction equation

HRID 410158 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[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:25]([C:26]#[C:27][Si](C)(C)C)=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)=[O:12].C(=O)([O-])[O-].[K+].[K+]>CO>[C:26]([C:25]1[C:20]([O:19][C:16]2[CH:15]=[CH:14][C:13]([C: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)=[O:12])=[CH:18][CH:17]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)#[CH:27]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59327100(1-Methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yloxy)phenyl)methanone

Product 1

HCID 59327156(4-(3-ethynylpyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1-Methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yloxy)phenyl)methanone (0.19 g, 0.44 mmol) and potassium carbonate (0.12 g, 0.88 mmol) was suspended in 1 mL MeOH. The mixture was stirred for 2 h at RT. Purification by prep-plate TLC (10% MeOH/DCM) afforded (4-(3-ethynylpyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone. MS (ESI, pos. ion) m/z: 354.0 (M+1). IC50 (uM) +++.

Workup

  1. customPurification by prep-plate TLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-17c02fa19ca145b2b2a0b13e774946d4
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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