Cesium carbonate → (S)-tert-Butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamate

HRID 598886Notes

Reaction equation

HRID 598886 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:18][CH2:19][C@@H:20]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)(=O)=O>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:18][CH2:19][C@@H:20]([NH:29][C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 163754-BromopyrazoleHCID 57950570(S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate

Product 1

HCID 57950651(S)-tert-Butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamateYield 93.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-bromopyrazole (1.26 g, 8.57 mmol) and cesium carbonate (4.66 g, 14.3 mmol) in DMF (20 mL) was added (3S)-3-((tert-butoxycarbonyl)amino)-4-(4-chlorophenyl)butyl methanesulfonate (2.70 g, 7.15 mmol). The mixture was stirred for 16 hours at room temperature. The mixture was diluted with DCM and washed with H2O (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (EtOAc/Hexanes, 0-25%) to give the product as an off-white solid (2.86 g, 93%). LCMS (API-ES) m/z: 428, 430 (M+H+).

Workup

  1. washwashed with H2O (2×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (EtOAc/Hexanes, 0-25%)

Sources & evidence

ORD record
ord-e76123ddf8244b0cbab98712674a6100
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…