Water → tert-Butyl 2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethylcarbamate

HRID 872499Notes

Reaction equation

HRID 872499 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].[H-].[Na+].CS(O[CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=O)=O.O>CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([C:12]2[CH:13]=[CH:14][N:15]([CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[N:16]=2)=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamateHCID 671687892-nitro-4-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 67172190tert-Butyl 2-(3-(4-cyano-3-nitrophenyl)-1H-pyrazol-1-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Nitro-4-(1H-pyrazol-5-yl)benzonitrile (1.0 g), DMF (10 ml) and sodium hydride (60% in oil, 0.24 g) were stirred for 30 min at RT. 2-(tert-Butoxycarbonyl-amino)ethyl methanesulfonate (1.45 g) in DMF (3.3 ml) was added and the mixture was microwaved for 30 min at 160° C. (Biotage Initiator Sixty operating at 2.45 GHz). After pouring the mixture to water, it was extracted with EtOAc. Combined organic phases were washed with water and brine, dried with Na2SO4 and evaporated. The product was triturated with IPA and filtered. Yield 0.92 g. 1H-NMR (400 MHz; d6-DMSO): δ 1.35 (s, 9H), 3.38 (m, 2H), 4.24 (t, 2H), 6.92 (m, 1H), 7.06 (d, 1H), 7.85 (d, 1H), 8.19 (d, 1H), 8.33 (dd, 1H), 8.70 (d, 1H).

Workup

  1. extractionwas extracted with EtOAc
  2. washCombined organic phases were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe product was triturated with IPA
  6. filtrationfiltered

Sources & evidence

ORD record
ord-df4e5720d6b8471f9758e1f707af85ab
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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