Cesium carbonate → Ethyl 3-(1-(4-bromobenzyl)-6-((5-methylpyridin-2-yl)methoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

HRID 1527723Notes

Reaction equation

HRID 1527723 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][N:38]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:36][C:37]4[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][N:38]=4)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 90411063Ethyl 3-(1-(4-bromobenzyl)-6-hydroxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 90410468Ethyl 3-(1-(4-bromobenzyl)-6-((5-methylpyridin-2-yl)methoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 10 mL round-bottomed flask were added a stir bar, ethyl 3-(1-(4-bromobenzyl)-6-hydroxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (100 mg, 0.23 mmol), cesium carbonate (227 mg, 0.69 mmol), DMF (2 mL), and 2-(chloromethyl)-5-methylpyridine hydrochloride salt (41 mg, 0.23 mmol). After 12 h, the mixture was partitioned between water (50 mL) and EtOAc (20 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (2×20 mL). The combine organic layers were dried with sodium sulfate, filtered, and concentrated to dryness (124 mg, 99%). MS (ESI): mass calcd. for C28H30BrN3O3, 535.15; m/z found, 536.1 [M+H]+.

Workup

  1. additionTo a 10 mL round-bottomed flask were added a stir bar
  2. customthe mixture was partitioned between water (50 mL) and EtOAc (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×20 mL)
  5. dry with materialThe combine organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness (124 mg, 99%)

Sources & evidence

ORD record
ord-df6022eedcc24211a5fd853f86b7ef79
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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